Skip to content

50+ fun Chicago restaurants: My guide for visitors & locals

fun Chicago restaurants

Time and time again I get asked for my reccomendations for the best restaurants in Chicago, but I’ve never actually taken the time to do a FULL round-up of where I think people should visit on a trip to the Windy City.

Well, that ends today!

I have spent HOURS on this post to ensure it’s one of the most comprehensive out there. 🙌🏼 (Seriously I just am ripping the band-aid off and hitting publish because I could spend weeks longer continuing to add to this list! 😬)

Of course, this guide isn’t JUST for visitors–whether you’ve never been to Chicago or you’ve lived here your whole life, I know you will find some good thought starters on this list next time you’re in search of a good restaurant.

This list has a little bit of everything for everyone, but I’ve curated it to showcase tons of various options based on what kind of experience you’re looking for.

Maybe you’re looking for the most fun restaurants in the city as a first time visitor.

Perhaps you’re in search for the BEST deep dish pizza and hot dogs (although that’s always a debate among Chicagoans 😉).

Or you’re looking for that elusive perfect spot the whole family will love?

Or the perfect place for date night in Lincoln Park?

Fine dining in the West Loop?

Or a great spot for BBQ and live music?

Top picks for a birthday dinner or other special occasions?

Or maybe where to get the best burgers (another contentious topic!) Even where to snag free kids meals?

Sometimes, you just need a great place close to your downtown Chicago hotel to grab a bite without having to snag a reservation.

I swear, I’ve tried to think of it all. 😂 So here is my BIG ole list of best eateries for any occasion you could possibly want! I’ve also included a table of contents to help you navigate this (very long) post!

50+ fun places to eat in Chicago + more FAQ’s

First, my favorite Chicago restaurants (reviewed in no particular order) and other fun spots

fun places to eat in Chicago

Bavettes (River North) 

Ask anyone who lives in Chicago at random where they would go for dinner if you gave them $200 on the spot, and they would all likely say “Bavette’s” without hesitation.

It is well-known to everyone as THE romantic spot for a date, the place you can get the best steak the city. (OK actually there are a lot of major contenders for that category that I will also list below, but the shoe-in answer is Bavette’s.)

They are also known for their fantastic pork chops, pasta, and great cocktails.

It is anything but a “steakhouse” vibe–it’s swanky, super dark and candlelit, with absolutely fantastic customer service.

Is it hard to snag a reservation here? Yes, so plan ahead.

However, if you’re solo or there are only two of you, it’s pretty easy to snag seats at the bar if you go early or late. The River North location is also easily accessible for those staying downtown. 

fun places to eat in Chicago

Boefhaus (Humboldt Park) 

Our #1 date-night destination of choice, and in my opinion, a rival to Bavette’s for the best ribeye in Chicago. However, they really have nothing else in common.

Boefhaus is a cozy, dimly lit American bistro with a few tables and arguably the best seats in the house are at the bar. If you want something low-key, unpretentious, but absolutely delicious, outstanding food–go here.

Might be a hike for you if you’re staying downtown, as it’s in Humboldt Park (not far from Logan Square or Wicker Park though!)

For a nightcap, hit Sportsman’s Club or if you’re in the mood for lived music, California Clipper (feels like you stepped back in time!) or Empty Bottle (the quintessential cozy dive music venue) down the street! You can’t not have a good time with that itinerary!

Mama Delia

Mama Delia (Wicker Park) 

One of our personal favorite wicker park gems. The atmosphere here is so fun and will transport you to Spain. The menu is Spanish so therefore very seafood heavy, but they have a great steak and great craft cocktails. After, make sure to go upstairs to the swanky burlesque bar! 

Lyra (West Loop) 

A West Loop Mediterranean spot with a swanky, buzzy atmosphere! A fun spot for a group, girlfriends or a night out with your date. 

Kaiser Tiger (West Loop)

One of our favorite casual spots when we lived in West Loop—what makes this spot fun is their big beer garden and curling lanes! (Making it a fun spot to go during the winter when you can’t stand being cooped up inside anymore). It’s also not too far from the United Center if you want to make a stop before or after a game or event. (It’s pretty far west, so you’re just a straight shot down Ashland.) 

Rose Mary (West Loop) 

Rose Mary is one of Chicagos best new restaurants (OK maybe it’s a couple years old now) by Chef Joe Flamm— a focus on Croatian fare (what they call “Adriatic drinking food”) great cocktails and fun atmosphere. It’s pretty hard to get a reservation here, so plan in advance, but again, when in doubt, you can always try for seats at the bar! 

BLVD: (West Loop)

BLVD: (West Loop) 

Another excellent choice if you’re in the mood for steak or seafood, and also the same owners as Rose Mary in partnership with Joe Flamm. The vibes are glitzy and swanky inside, and a fun, more casual breezy patio on the outside. This would be an especially fun place to come with a bachelorette party and it’s easier to get reservations here. 

Cafe BaBaReeba (Lincoln Park) 

A Lincoln Park gem loved by all, this was one of the first restaurants I ever ate at in Chicago and it still holds up.

The laid back, homey atmosphere makes you feel like you’re pulling up a chair at your Spanish neighbors house.

The menu is traditional tapas fare, but what might surprise you is that they’re also famous for their tapas brunch!

Gilt Bar (River North): 

Gilt Bar doesn’t always get the credit it deserves because it’s always in the shadow of next door to Bavette’s, but they have great food (think a classic upscale American menu).

Their main dining room is dark, romantic and swanky, so it’s a great place for a special occasion or a date just because, but the real gem is their basement lounge with great live music. 

fun places to eat in Chicago

Chef’s Special (Bucktown/Logan Square) 

If you love Asian food and creative cocktails, you cannot miss Chef Special. Everything we ordered was SO good. We didn’t have a reso on a Friday night but we were patient and snagged seats at the bar. Just ask for their guidance with the menu based on what you like, you can’t go wrong. 

Gejas: (Lincoln Park) 

You will not see Gejas on any list of trendy Chicago restaurants, but if you’re in Lincoln Park and happen to want a little kitsch and something out of the box, this fondue restaurant is one of the best places you could go, in my opinion. Very unassuming on the outside, and inside, it’s a candlelit cavernous basement and both the cheese and meat fondue are delicious, and of course, the chocolate fondue for dessert!

Gemini Bistro: (Lincoln Park) 

Speaking of Lincoln Park, if you’re in the mood for something a bit more classic and upscale, Gemini bistro might be the ticket for you.

Fun fact, I used to live across the street. It’s a restaurant very near and dear to my heart.

The neighborhood bistro all the locals love.

Great service, outstanding food and cocktails. (They make my favorite Sidecar in the city!)

Great for a date, but you’ll always find families in here as well. If you’re up for a nice walk before or after dinner, you can stroll through the (free) Lincoln Park zoo nearby and catch views of Lake Michigan.

In the winter months (late November through January) they have Zoo Lights at the zoo, and this is a fun place to come before or after!

Green Street Smoked Meats (West Loop): 

As the name suggests, meat lovers, this Texas-style BBQ restaurant in West Loop is your spot. If you’re looking for a no-frills casual dinner with really really good food, you will find it here! It’s basically a rustic-chic BBQ cafeteria–grab a metal sheet tray and knock yourself out–everything is a la cart!

Punch Bowl Social (West Loop)

I wouldn’t normally throw this on a “best restaurants” list, but I often get asked for recommendations that can suit a big group/ entire family (21+ starts at 9pm, until then, bring the teenagers). It’s also a go-to for groups from birthday parties to work events, so if you’re with a lot of people, this could be a good spot! 

What’s so cool about it? It’s a 30,000 square foot converted meatpacking warehouse–it has everything from bowling to darts, giant jenga, bocce ball, ping pong, and more–plus karaoke and vintage arcade games–plus a full bar and full menu of apps, entrees and more.

Ada Street (Bucktown)

Getting here and thinking your Uber driver is taking you in the back of Home Depot to murder you is all part of the experience of going to Ada Street.

Don’t worry though, as soon as you walk through the nondescript door you’ll be greeted by a long, dark, candlelit hallway with vinyl playing in the background.

It’ll open up to Ada Streets unassuming but charming, low-key, and romantic dining room with a big ole open garage door (in the summer).

The food is always seasonal, fresh, creative but homey.

Every wine I order here is my new favorite wine.

I love, love, love Ada Street. I’ve never had anything less than a wonderful meal here.

(Also, they have a small private room, so fun for groups too!)

Duseks and Punch House (Pilsen)

If you want to venture out of downtown and into a local neighborhood with a ton of character, Pilsen is a very fun spot.

During the day, don’t miss the incredible authentic Mexican food, the vintage shopping and their plethora of graffiti art. (You can even take a street art tour!) but at night, don’t miss Thalia Hall–one of the best intimate concert venues but also the building houses Duseks–one of our favorite go-to restaurants (that is often pretty easy to get into last minute) and their two bars–the basement 70’s punch bar Punchouse, and the piano bar Tack Room.

You can spend all night here and don’t ever have to walk outside. (Which is why it’s often a go-to in the winter months–not that it isn’t fun in the summer months, too!) 

Untitled (River North)

If you’re wanting buzzy clubby vibes, but not QUITE that turned up–Untitled is where you go. It’s a massive swanky underground restaurant and lounge. This is also a good spot for large groups. Every Wednesday-Sunday they have live burlesque aerial performers, jazz musicians and more. 

Le Colonial (Gold Coast)

OK I know I’m getting a little repetitive because I keep saying so many of these are one of our personal top favorites and they are. But if I had to pick ONE restaurant in the Gold Coast or in the entire downtown vicinity, it would be Le Colonial. They moved locations recently and it’s the most beautiful setting!

I’ve never been to Vietnam, but it certainly feels like you’re transported the minute you walk through the door. No detail is overlooked, and the food is incredible. Don’t miss the fried rice (sounds like such a vanilla order, really, but trust me) the crispy rolls, the beef pho. It’s all great.

And make sure you start or end (or both?!) with a Lychee martini.

Now I’m dying to go again. 😂

Kit Kat Lounge & Supper club (Lakeview) 

Another fun Chicago must for most fun people–Chicago’s favorite spot for dinner (or brunch!) and a drag show! it’s worth the trek to Lakeview even if you’re staying downtown! They also have the most extensive cocktail list I’ve ever seen–martinis are in order!

Chicago Athletic Association: Cindy’s Rooftop, Game Room, Cherry Circle Room (South Loop)

A historic hotel that houses some really great restaurants and bars! Also conveniently located near the Art Institute and Millennium Park so it’s fun to hit Cindy’s for brunch before, or Cindy’s, Cherry Circle room or even the game room after! The Game room is a bar that has all kinds of classic games. (But I believe it’s 21+!) 

Armitage Alehouse (Lincoln Park) 

I almost didn’t include this one because it’s nearly impossible to get a reservation, but if you plan far enough ahead (truly, set your timer when they release the dates–more info on their website) otherwise, it’s totally worth trying to go at 5pm or late night to see if you can sneak in and grab seats at the bar or a walk-in table! You MUST sit inside–the ambiance is so cool. Old English Pub vibes serving up amazing Indian-inspired dishes.

Carnivale (West Loop) 

Speaking of ambiance, Carnivale has a ton of it. Lively and colorful with fun cocktails and great food from South America, Spain & the Caribbean. Dinner here feels like a giant party! 

Aba (West Loop) 

Again, I’m getting a little repetitive here because I’m running out of ways to describe West Loop restaurants. They’re pretty much all impeccable, on theme, swanky with great food, etc. Aba is no different! If you’re in the mood for some delicious fresh Mediterranean small plates and a great rooftop (plenty of room inside and they have igloos outside in the winter!) go here! Don’t miss the short rib hummus!

Tortoise club

Tortoise club (River North) 

If an old-school steakhouse that transports you back in time (truly, you can’t tell what decade you’re in when you go in!) this is it. It’s just the best. White tablecloths. Oysters. Great service. The whole 9 yards. Get a delicious steak, sides, and of course–a martini. (You have to!) They also have live jazz in the bar on Saturday nights. (I would call or check the website to confirm the schedule though!)

Au Cheval (West Loop) 

Like Bavette’s (coincidentally, same ownership!)–ask any Chicagoan what the best burger in Chicago is and they will all likely say Au Cheval. There are like 5 total things on the menu, but just get the burger and duck fat fries and you’ll thank me later! Tip: Get here early, put your name in, and head to Lone Wolf for a drink, and they’ll text you when your table is ready! Expect a long wait for dinner, but they’re also open for lunch! 

Girl and the Goat (West Loop) 

This is such a special restaurant (in general, but particularly to me). Many years ago, Chef Stephanie Izard opened her very first restaurant with the famed Boka restaurant group after her Top Chef Season 4 win (do you remember that season? I remember it SO well!)

I was such a big fan of hers and then I moved to Chicago right after collage and I remember getting to come her for the first time when I was probably 23–I was totally star struck to be in her restaurant and felt like “holy shit, I have made it in life–I live in the big city and I’m at Stephanie Izard’s restaurant!) It was the first time I had ever had that kind of food–creative and upscale but casual and unpretentious (the kind of food Chicago restaurants are known for). I was FLOORED.

This is also the restaurant that put Randolph Street (AKA Restaurant Row) on the map as the hub of the best restaurants in the city (and the world, truly). G&G is the OG–so eating here is basically experiencing a piece of Chicago’s culinary history! 

Tip: There are four counter seats overlooking the kitchen and they’re the best seats in the house. I’ve never sat there but have always wanted to! Also, if you can’t get a reservation or want to walk in, go early or late and you should be able to snag bar seats if you’re patient! 

Beatnik on the River (River North/River walk) 

Chicago has put a lot of funds into their riverwalk in recent years and it has definitely paid off!

One of the best spots on the riverwalk is Beatnik–a funky, boho-chic restaurant with a globally-inspired, veggie-forward menu. Perfect especially in the summer months! 

3 Arts Club in Restoration Hardware (Gold Coast) 

What’s more fun than grabbing coffee or lunch in a stunning atrium of a wildly expensive furniture store!? NOTHING!? Just trust me, it’s a worthwhile experience! 

Summer House Santa Monica (Lincoln Park) 

Okay there are more “Chicago”-like restaurants than Summer House, but I think it’s worth putting in here if you happen to be visiting in the winter because its the closest thing us midwesterners are going to get to a California experience.

Somehow it really DOES feel open-air breezy in there even in the dead of winter. (I’m not one for themed restaurants but this really doesn’t feel like a breezy Cali theme!)

You can expect delicious California fare–salads, sandwiches and pizzas. Also definitely don’t miss their sea salt chocolate chip cookies!

Wiener’s circle (Lakeview)

If you’re looking for a Chicago-style dog and a wild experience, go here at night. Order a Chocolate Shake and ask for ketchup on your hot dog. Expect lots of verbal abuse and the most hysterically rude customer service you’ve ever experienced in your life. 😆 (It’s a bit, it’s what they’re famous for.)

Not for the faint of heart but I can’t think of a better way to end the night out. 

Andros taverna (Logan Square) 

Are you sensing a theme here? Chicagoans like restaurants that feel like warm escapes. 😂 Andros is one of Logan Square’s newer restaurants and it will take you to Greece.

The interior is beautiful, the menu is so fresh and flavorful, and they have an AMAZING wine list full of interesting wines!

Portillos (River North)

Another famous Chicago staple and where you should come for your Chicago hot dog or Italian Beef sans verbal assault. (My brother in law, Brendan, loves their chicken tenders also, so rest assured–the menu is ) If you love a chopped salad–they’re also famous for that, too! (It’s so good!)

90 Miles Cuban Cafe (Logan Square)

Amazing BYOB Cuban with a festive mom and pop feel. This is especially fun in their summer months to sit on their open air patio under the string lights, but a visit in the winter months will transport you far away and is such a fun escape! 

Irazu (Bucktown)

Another fun, low-key, casual BYOB gem nearby. What Irazu lacks in space it makes up for in flavor. If you’re in the mood for some Costa Rican food (or want to try some for the first time!) I can’t recommend this locally loved spot enough.

Big Star (Wicker Park)

A well-loved Wicker Park institution with killer margaritas and street-style tacos. The best Mexican food is in Pilsen, but Big Star is where the vibes are! (Family-friendly too, but note, they don’t have high-chairs.) 

Park and Field (Logan Square) 

Always a fun pick in Logan Square with tons of picnic tables, Adirondack chairs, and fire-pits. A great place to post up with friends! (Or kids!)

Momotaro (West Loop) and Izakaya (downstairs from Momotaro): 

I don’t even like sushi and I LOVE the menus at Momotaro. Described as “multi-dimensional Japanese dining.” Momotaro is fine-dining without being stuffy or pretentious and they have something for everyone. Downstairs is their Izakaya, which is focused on casual street food! (I haven’t eaten there, but heard good things!) 

Qing Xiang Yuan Dumplings

Qing Xiang Yuan Dumplings (Chinatown) 

If you’re looking to venture away from the trendy downtown restaurants and are in the mood for some dumplings, look no further than this gem in Chinatown.

Neal, June and I came here for mothers day lunch and it was so much fun. Worth the wait–get there early to put your name in, and then go walk around and explore Chinatown! (Get some coconut buns at one of the local bakeries–so good.) It’s in a shopping center not a far walk from the main drag but it’s worth walking down the street to explore all of Chinatown. The restaurant itself is a small, busy, buzzing space with quick service (making it good for little kids, too).

I know you won’t have a bad time here!

Dim Sum at Triple Crown  (Chinatown) 

Traditional Dim Sum in Chinatown is always the most fun experience, and I always send people to Triple Crown! Another alternative is Phoenix, which is equally as good, but I love that Triple Crown is on the main drag of shops and restaurants. Get a coconut bun from any of the nearby bakeries for dessert!

Trivoli Tavern (West Loop)

Another one owned by Hogsalt (of Bavette’s, Au Cheval, Armitage Alehouse, and Gilt Bar) so you KNOW it’s got fantastic food and ambiance. Ask to be sat on the floor of the main dining room (definitely the best seats in the house IMO).

Eataly fun places to eat in Chicago

Eataly (River North)

If you’re a foodie and lover of ALL the Italian foods, groceries, specialties, and the like, you must go to Eataly! It’s a fun place to shop for amazing quality Italian goods, groceries and wine, and grab a drink, some small bites, a scoop of gelato, espresso, or a whole meal. (They have changed things since the pandemic, but they currently have two restaurants open!)

It’s extra fun during the holidays where they always have the upstairs decked out. (One year it was an Italian Alps theme!) You can also take cooking classes here–there’s always something fun to do.

Lou Malnati’s for deep-dish pizza (lots of locations)

Hands-down the best deep-dish and I will not hear other opinions on the matter. 😉 Truly though, I really do think it’s the best. (Yes, people are die-hard about Pequods, but I’m not a big fan.) They have a bunch of locations and it’s a great spot for the whole fam.

Parson’s Chicken & Fish (Logan Square, Lincoln Park, West Town)

The OG spot for the best chicken sandwiches in Logan Square! Such a fun atmosphere with picnic tables, umbrellas, and their famous Negroni plushies! Anything chicken-related here is delicious–chicken strips, nuggets–whatever. Their salads are good too! 

Purple Pig (Magnificent Mile)

While the Mag mile is known for its shopping, it’s not exactly famous for its world class restaurants–except for the Purple Pig, which some would argue rivals any trendy spot in the West Loop. (Though I’ve never been, I’ve had countless people rave about it to me–so I wanted to mention it here because I know so many people stay on Mag Mile and are always looking for nearby spots to go!) 

Club Lucky (Bucktown)

Speaking of family friendly, this is one of our favorite spots to take June, but also, has been one of our favorite neighborhood Italian restaurants long before we had her! Our favorite is to sit in the bar area, either at the bar itself or one of their few booths. (Best seats in the house!) They also have a big patio during the summer.

Eating dinner here feels like a hug, and you will definitely leave with leftovers! The menu features a big list of Italian-American specialties–my favorite being the chicken marsala, fettuccini Alfredo, their famous tortellini.

Their pork chops are also excellent and don’t miss my two favorite salads: the Club Lucky salad (ask for it chopped) or the Meatball salad. (Sounds a little odd, but so good.)

Also, one of the best dirty martini’s in the city! (Don’t miss their hand-stuffed blue cheese olives!)

Gyu Kaku (West Loop) 

A fun, interactive experience–grilling right at your table. Japanese BBQ doesn’t disappoint whether it’s for a date, or with family. (Definitely a hit with kids of all ages!) They have multiple locations too!

Twin Anchors (Old Town)

Famous for its delicious ribs, fun old-school atmosphere and being a frequent hangout of Frank Sinatra back in the day. If you’re seeing a comedy show at Second City, I always recommend coming here after! 

RL Restaurant

RL (Ralph Lauren):

The iconic restaurant in Ralph Lauren is not to be missed, and make sure you plan in advance.

If you want to channel your inner old rich lady (and who doesn’t, honestly?) this is your jam. The inside is exquisitely decorated and so cozy (it’s a favorite of mine in the winter months) you’ll never want to leave.

Get yourself a glass of champagne, a fancy club sandwich or the burger–fries are a must, too, of course!

Don’t leave without a walk through the giant Ralph Lauren store. (I’m not one for designer stores because I feel like they can always smell that I can’t afford to buy anything 😂 but they aren’t snooty here. They know they’re part tourist attraction, part retail destination.)

Lonesome Rose & Golden Teardrops (Logan Square)

A great spot for tacos in Logan. The perfect mix of casual/trendy/vibey while still feeling very quintessential Logan Square. We often sit at the bar here! Tip: A big part of the draw here is their lesser-known downstairs speakeasy, Golden Teardrops, where you must go for a nightcap!  

Smoke Daddy BBQ

Smoke Daddy BBQ (Wicker Park)

If you love BBQ and live music, you will love Smoke Daddy. It’s not a big space, but it has a lot of personality, and the food is fantastic. It’s also kid-friendly and I believe they have certain times/days that kids eat free (worth calling to ask). They have a great open-air patio, too. Go across the street to Vinny-D’s after for some ice cream, snow cone or Italian ice! 

Le Bouchon: (Bucktown)

Can’t make it to Paris? Le Bouchon is the next best thing!  A tiny bustling French restaurant with the most delicious comforting classic French food. Plan ahead to snag a reservation–they only have a few seats at the bar, so not an easy place to walk in! 

Osteria Langhe

Osteria Langhe: (Logan Square)

If you’re in Logan and in the mood for a cozy romantic dinner and some incredible, authentic Northern Italian food–go to Osteria Langhe. Don’t miss the Plin! 

FAQ’s: More questions about where to eat in Chicago: 

I’m only in Chicago for a day trip–it’s my first time, what should I do!? 

For first timers (or anyone who has never done it before) I would definitely hit an architecture tour from the Chicago Architecture Association on the Chicago River!

This is a great way to not only get a feel of the history of the city but it’s the best way to see all of downtown from the water. The boat has a top deck and also an indoor portion, so I still think it’s worth going if it’s not great weather!

Walk the Mag Mile to the Gold Coast will give you a fun feel of the city and great shopping, then, snag an outdoor table at any of the restaurants on the triangle in the Gold Coast for lunch or a drink (locally referred to as the “Viagra Triangle”) The people watching here is one of my favorite things to do. (LuxBar, Gibsons and Hugo’s are all great options. They have heaters and tents in the winter as well!)

For dinner I would go somewhere in the West Loop where a ton of the best restaurants in the city are all a few blocks from one another. Go to Grapes and Grain (a great piano bar) for a nightcap.

Another great option (one of my favorites) for lunch and dinner downtown is RL (Ralph Lauren) but you’ll want to make sure to book a reso in advance!

Tea at the Drake or the Peninsula is also an iconic experience!

It’s Saturday night and I’ve made no reservations, where can I get in!?

Chicago has become tough for dinner resos lately. My best advice is to either eat before 6pm or after 9pm (9:30 or 10 is even better–bar hop and get an app or two for a couple hours beforehand to tie you over). Also, it’s much easier to be patient and snag seats at the bar somewhere vs. wait for a table.

Three gems I’d recommend that seem to always have availability:

Bistronomic in the Gold Coast, Duseks in Pilsen, or downstairs at Smith & Wollensky (the more casual Wollensky Grill)–it’s a hidden gem that has great views of the river, too.

Make sure to browse Resy and Opentable, but also, if there is somewhere you have your heart set on, give them a call. You’ll often find that restaurants looked booked online but if you call, they may be able to squeeze you in!

Where can I eat near Wrigley field? 

I’m not the best person to advise on this because I’m not that familiar with Wrigleyville, but if it’s a game-day, be warned: it can be a frat party. 😂 Anytime there is an event or game at Wrigley field, it’s a zoo.

But, if you’re a big cubs fan and are looking for a sports bar, Budweiser Brickhouse is a big sports bar next door and has views of the field.

If you’re looking for a great dinner option (say, before or after a concert at Wrigley Field or something) Tango Sur is amazing and BYOB! Smoke Daddy also has a location there (my favorite BBQ spot!)

Where should I eat on Navy Pier?

You shouldn’t. Find a better place to eat. Chicago is one of the most amazing culinary destinations in the country. PLEASE don’t waste one of your few Chicago meals at Navy Pier. Where to go instead? River North and the Gold Coast are both quick Uber rides from Navy Pier and it’s worth taking the extra effort to go there for a great meal.

(It’s probably important to know that Chicagoans famously loathe Navy Pier the way New Yorkers loathe Times Square, but Navy Pier has none of the iconic excitement that Times Square does, so in my opinion, it’s way worse. 😂)

Of course, it is a family friendly destination with the Ferris wheel, the Children’s Museum, etc. So it’s understandable why you’d want to make a visit. That being said, anyone who lives here will tell you to get off the pier as it will allow you to avoid the crowds and enjoy MUCH better food.

However, if you insist on eating near or on Navy Pier, Giordanos is a solid family friendly option, so you could knock out your deep-dish experience there. (I prefer Lou Malnati’s but many locals would argue Giordano’s is their favorite–so you really can’t go wrong!)

They also have a giant rooftop restaurant (the largest in Chicago) called OffShore that overlooks lake Michigan.

Another option if you’re in the mood for a good burger is Billy Goat Tavern on the pier–also a Chicago institution (the one in River North that is).

There are also some great ice cream options there too! Rainbow Cone (a Chicago staple) and Kilwins! 

Where should I eat near Willis Tower or the Hancock Building?

Near the Hancock: anywhere in the Gold Coast or River North are quick and easy to get to. (I’d go for Le Colonial if you can, but lots of other reccos on this list in that vicinity too!) For the Willis (Sears) tower, dining anywhere in West Loop is a great bet. (Again, lots of options on this list in West Loop!)

What are the best family restaurants in Chicago? Anywhere great for babies? 

Chicago is full of family-friendly options. I have a whole blog post on where to eat in Chicago with kids and babies right here!

Some our go-to’s: Our ultimate favorite is the Perch–and kids eat free here every day from 4pm-6pm! Smoke Daddy is another favorite (same owners!) as is Big Star (heads up: they don’t have high chairs) and Parlor Pizza (they don’t allow strollers inside, but they have a stroller parking area outside!)

TBH, most places are easy with kids around 5-6pm before the dinner rush.

I’ve said this a lot, but I’ll say it again: one of the best things about Chicago is that it’s just un-judgey. I’ve never felt judged for taking June out to dinner anywhere. Most places are very accommodating!

Would I take her to a Michelin star restaurant? Probably not–but use your best judgement.

General rule of thumb: call ahead to confirm if they have high chairs, get there at 5 to give yourself lots of time before the rush hits, and you’ll be great. 

Best deep-dish pizza and hot dogs?

Easy. Lou Malnati’s for pizza and Portillo’s for hot dogs. BOOM.

Best rooftop bars in Chicago that I can’t miss? 

Rooftops and patios are one of the great things about visiting Chicago! I have a whole blog post on Best Chicago rooftops and patios.

Where should I eat before a Broadway show?

BLVD in West Loop is a go-to for us before shows because it’s just a quick zip down Randolph to get to a lot of the Broadway theaters. Carnivale would also be easy, Proxi and Sepia also good options, or Gibson’s Italia is nearby the Theatre district.

In the South Loop, any of the restaurants in the Chicago Athletic Association or The Gage would be easy to get to the Theatre district.

If you want to walk (not Uber) I’d go Chicago cut (iconic Chicago steakhouse) Beatnik on the River, Tortoise Club, or the closest option, Petterino’s in the theatre district, is also really old school and fun–it isn’t somewhere I would seek out if not before a show, but will give you a fun old-Chicago experience with it’s red booths, white tablecloths, steaks, chops, and more.

Where should I eat if I’m planning a trip the Art Institute of Chicago, Shedd Aquarium, Field Museum, Planetarium, Soldier Field or Museum of Science and Industry? 

These areas aren’t really known for great restaurants, but a nearby gem not far from museum campus/Soldier Field if you love an Irish Pub, is Kitty O’Sheas! The Gage and the restaurants in the Chicago Athletic Association are a great pick if you don’t mind a quick Uber (just a straight shot up Michigan, but definitely walkable from the Art Insittute) or you could jet over to Chinatown for dumplings or dim sum! 

Best Michelin-starred restaurant in Chicago? 

The #1 Michelin-starred restaurant in Chicago is Alinia. I will tell you that fine dining is absolutely not my thing so I can’t speak to that specifically, but it’s the only three Michelin star restaurant in the city. Ever might also interest you as the fine dining restaurant Richie worked at in The Bear!

What should I wear out in Chicago at night? 

Anthony Bourdain once described Chicago as a “no-bullshit city,” and I think that’s very true. Nobody is going to judge you for wearing whatever you want to wear here!

I’ve never heard of someone being turned away from a restaurant because they weren’t “suitably” dressed.

That being said, I usually love a dressy-casual outfit for going out at night–jeans, a top, maybe heels (or not), a leather jacket, some lipstick. In the summer months, a cute sun dress, maxi dress, and flat or heeled sandals. Cute, but nothing too fancy! I have tons of outfit options right over here and on my LTK page! 

These posts might also help: Winter date night outfit ideas + Summer date night outfit ideas + What to do and wear in Chicago in the winter

I hope this gave you a VERY comprehensive list of Chicago restaurants to check out! Have the best time!

You might also like: Fun Chicago date night itineraries