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Best Day & Weekend Getaways from Chicago

Summer outfit for a weekend getaway

Similar linen button down, similar shorts, sandals, similar hat, Ray Bans, Lo & Son’s Catalina weekender bags (white is “tote” size–which was my Italy carry-on and grey is “deluxe” size! We are officially OBSESSED and can’t recommend them enough!) 


Can you believe it’s almost MID AUGUST?! WHAT?!

Luckily Chicago summers last pretty much into October so this at least makes me feel a little bit better.

Do you have any fun getaways planned coming up? Are you itching to get out of the city?

Neal and I checked out a Jeep Wrangler from Zipcar this past weekend and drove it to the lake house in Beverly Shores–it was a nice little change of pace! (Especially because we’ll be traveling a lot over the next month, it was great to get out of the hustle of the city for some peace and quiet!)

Did you know Zipcar just added Jeep Wrangler’s to their fleet!? I have ALWAYS wanted a Wrangler–my dad had one when I was growing up–I loved going for drives with him and our Jack Russell Terrier, Zia–they’re some of my favorite summer memories as a kid. Turns out, they’re still just as fun to drive and they are perfect for a day trip or weekend trip out of the city!

This is the inspiration behind today’s post–sometimes you just need to get out of the city to explore, experience something new, and go on a quick adventure that doesn’t require a plane ride or a passport.

Luckily, there are so many places to get out of the city that don’t require a ton of travel time and I’ve compiled them all right here! Keep reading for some of the best quick trips to take outside of Chicago.

Best Weekend Getaways from Chicago

Best Day & Weekend Getaways from Chicago

Chicago style blogger shares a list of the weekend weekend getaways for people living in the Windy City

Warm Weekend Getaways (and day trips, too!)

There are SO many places to get away from the city in the warm weather. From spas to lakes, outdoor activities, hiking, beautiful resorts with pools and more, these are some awesome places to go during the summer or spring that are only a quick drive away! (Seriously, most of them are only an hour and half–up to 3 hour drive at most!)

Best Day & Weekend Getaways from Chicago

Chicago Lifestyle blogger weekend trips with Car2Go

Indiana Dunes: Great for Day trip or Weekend

This is where we always go–there are quite a few lakeside towns that comprise “The Dunes” but Beverly Shores is where we always go as Neal’s family has been going up there for years! It’s very beautiful and scenic, steps from Lake Michigan, and very quiet (we’re talking like, a gas station and one restaurant) but it’s very peaceful surrounded by woods, a marsh, and easy access to the lake.

If you want more action (i.e. more things to do), definitely check out charming Long Beach (which is nice because you can rent a house that is actually on the beach, whereas in Beverly Shores, the homes have no beachfront access–they’re all a short walk) or there is Michigan City!

There’s also New Buffalo (not in Indiana, but Michigan) is also very close by and is an awesome place to stay–they have an adorable little town, lot’s of restaurant and lodging options, and several wineries, which makes it popular for vacation as well as bachelorette parties.

The best part about visiting any of these spots is that they’re only about an hour and a half drive from the city–making them great for a day trip or a weekend! You’ll feel a million miles away from the chaos of the city, but you won’t waste much time driving there!

If you’re the outdoorsy type, the Indiana Dunes State Park is also a great day trip from the city–there’s lot’s of beautiful hiking trains!

A couple of my favorite spots: Chesterton European Farmer’s Market, Joe & Freddy’s, Goblin and the Grocer, Froehlich’s in Three Oaks for lunch, Redamaks for burgers in New Buffalo, vintage shopping at the shops on Red Arrow Highway.

Chicago Weekend Getaways

Above: Main Street in Galena–the most adorable town! 

Galena: Best for a night or weekend

Neal and I visited Galena a few months back and we can’t wait to visit again. It’s about a three hour drive from Chicago and was so cute, charming, and full of so much history! It’s actually perfect for a weekend trip year-round (more on that below)–we really want to visit again in the fall when the leaves change because it’s so beautiful! You can read our whole Galena, IL guide in this post! 

Lake Geneva and Lake Delaven: Great for a weekend

I absolutely LOVE Lake Geneva and Lake Delaven–both are neighboring lake towns about an hour and a half North of Chicago. There are so many hotel options in both spots (check out Grand Geneva Resort and Spa!) or vacation rental options (like this one, it looks amazing and right on the marina!) The town is absolutely adorable with lot’s of cute shops, restaurants, and bars. We’re heading up to Lake Geneva in a couple weeks to visit our friends Pete and Sheryl and we are so excited!

We’ve also stayed at Lake Lawn resort on Lake Delaven for my friend Leigh’s wedding and it was so much fun–it felt like we were in Dirty Dancing! They have multiple pools, restaurants, bars, and so many fun activities! If you want a fun destination that is beautiful and surprisingly reasonably priced, definitely look here!

Things to do on the weekend in Chicago

Milwaukee: Great for a Day Trip or Weekend

I think Milwaukee is one of the most underrated midwestern cities. I have no idea why Chicagoans don’t go up to Milwaukee more–it’s only about an hour and a half away! I’ve spent so much time in Milwaukee and I discover new amazing things to do there every trip. (My best friend Kate’s parents live there, and we go visit them often!)

Milwaukee is especially fun in the summer because you can rent a pontoon boat and cruise up and down the river–there are several bars you can dock at, hopping on and off the boat all day! (Just make sure you have a sober driver!) This is what we did for my bachelorette party and it was so fun.

I would recommend finding a hotel (there are some really nice ones!) or a vacation rental in the Third Ward–this is my favorite part of Milwaukee and so much is within walking distance.

Another great part about Milwaukee is that there are a lot of lakehouses that are just a few minutes from downtown, so you can have the best of both worlds! We recently stayed on Nagawicka Lake for my friend Melissa’s bachelorette party and it was amazing!

Some can’t miss Milwaukee spots:

The Milwaukee Public Market (my favorite market EVER! They have so much good stuff to be found here!) For restaurants,  La MerendaOdd Duck, Barnacle Buds, Harp (both great dives) Camp Bar, Balzac, Lakefront Brewery (do a tour!), also the the Milwaukee Art Museum, and of course Miller Park for a Brewer’s game.

Jeep Wrangler Car2Go

Southeastern Michigan:

I highly recommend checking out the areas of South Haven, Saugatuck and Fennville. Such a beautiful area with so much to do! We love Modales winery, Virtue Cider, and all the restaurants, bars and shops in town. For the past couple years we’ve been renting this amazing house in South Haven with a bunch of our friends and all the kids–while we don’t leave the house much (😂)  it’s a beautiful place super closet to the beach and a great family friendly spot for a reunion! Another amazing spot to stay in the area is the Fields of Michigan! You can see my review and South Haven guide right here!

Kettle Moraine State Park, Wisconsin (great for a weekend) 

Last summer we planned a camping trip to Kettle Moraine State Forest (we stayed at the Ottowa Lake campground) and it was one of the highlights of the summer. It was our first camping trip with June (of course it was not without its hiccups) but it was the perfect family-friendly camping spot and an absolute gem of a place to spend a summer weekend. You don’t have to camp to enjoy this area–you can easily find a vacation rental nearby. We loved the family-friendly beach at Ottowa Lake and the nearby Scuppernong hiking trails! If you’re looking to get off the grid during the summer (but not TOO far off the grid) this is the perfect place to do it as it’s only about 2 hours from Chicago!

Cold Weather Weekend Getaways:

Speaking of Southwest Michigan–this is actually a great place for a winter escape, too! I think there’s something magical about cozying up in a secluded cabin in the woods during the freezing months, so I highly recommend staying in Fennville. (We rented this little cabin on the river!) It’s still a quick drive to Saugatuck and plenty to do there during the winter.

Here are some other cold-weather weekend getaways from Chicago that are on my list, perfect for cozying up by the fire, hitting the spa, or the slopes!

Chestnut Mountain Resort (Great for a weekend!)

Galena’s ski resort, which I’ve heard really great things about! Not that Illinois is famous for its skiing, but Chestnut Mountain resort is a ski-in/ski-out resort that is supposedly very fun! When we visited Galena a few months back, a couple of you guys messaged me on instagram saying you love skiing at Chestnut Mountain!

The American Club at Kohler, WI (great for a weekend):

I have been dying to go to Kohler FOREVER. It’s an amazing destination year-round, but I think it would be especially cozy during the winter. Their lodge is gorgeous, they’re known for their luxurious spa, and they have lot’s of cozy restaurants and outdoor activities like ice skating, snowshoeing, and clay shooting!

Alpine Valley (great for a day or weekend): 

Yes, this is the Alpine where you probably saw Dave Matthews in high school–but it’s a ski resort during the winter. Neal and I went with some friends when we first started dating and it was a blast. Yes, it’s more of a “big hill” than a mountain, so those who are used to skiing out west might need to adjust their expectations accordingly, but it’s fun just the same. They have a lodge hotel where you can stay overnight (it looks like a nordic-themed Chalet which is adorably kitschy). It seems like reviews on the lodge are a bit mixed, but if you want a budget-friendly getaway with friends, this fits the bill! Otherwise, there seem to be some cute Alpine Valley vacation rentals in the area to choose from! (How charming is this A-frame cabin!?)

Best Day & Weekend Getaways from Chicago

How to get there:

You definitely need a car to visit all of these destinations, and if you don’t own one, Zipcar makes it easy to plan a quick weekend getaway from Chicago–you can rent by the hour, or by the day–which makes it a great option for those who don’t have cars in the city! Plus, they now offer Jeep Wranglers as part of their fleet in select cities–basically the BEST car for all your weekend getaway adventures this summer! Is there anything better than blasting your favorite tunes with the top down?

On the flip side, they have several all-wheel drive SUV’s and sedans that are ideal for winter road trips!

Bonus: If you sign up for Zipcar through this link, you’ll get a free month trial, waived membership fee, and $25 in free driving credit!

Zipcard Jeep Wrangler Zipcar

Jeep for a weekend getaway in Chicago

How Zipcar works:

Essentially, it’s a car sharing service that has cars ALL over the city. (They have a map you can look up on their website that shows you where the nearest Zipcars are. You’ll likely find several within walking distance! We picked up our Wrangler in Wicker Park off of Division street!) When you sign up you’ll be mailed a Zipcard. Which is essentially what you use to lock and unlock the car! It’s so cool!

You just look up what car you’d like online, reserve it, walk there, pop your Zipcard over the sensor, and it’s magically unlocked for you to grab and go! It’s essentially access to a car on demand, with none of the hassle that comes with owning a car.


You pay a small monthly membership, starting at $7/month, or you can pay upfront for $70/year. To reserve the car, you pay an hourly fee, ranging from $8-$14 per hour (based on the size of the vehicle). You can reserve it for an hour or a full a day starting at $74. Which is great for getaways up to 180 miles outside of the city! The rates start at $80/day. Rates vary based on what kind of car you need, where you live, etc.


The cool part is that they offer so many models of cars–again, Jeep Wrangler for a trip to the lake? You can do it! All wheel drive SUV for the slopes? Sure! A BMW to make those boring errands more fun? You can! Prefer a hybrid? Take it for a test drive to IKEA! It’s awesome!


It’s also worth addressing three car-ownership pain points: gas, insurance, and IPasses.

First, with Zipcar, your gas is covered. You do not have to pay anything extra for gas. (Which is around $3.39 per gallon right now in the city!) If you do need to fill up the car, there’s a gas card you can swipe–no extra cash out of your pocket! (Depending on how far your trip is, this savings could easily pay for itself!)

Second, insurance–you’re covered with liability insurance and you have the option to purchase additional insurance for a few extra dollars a month that would waive any additional damage costs should you get into an accident. It’s a pretty great deal–you can see all of that nitty gritty right here.

Third, their cars include IPasses! This means you won’t get ticketed if you forget to pay your toll online when going through an IPass lane (I can’t tell you how much money I’ve thrown away this way ?) AND you don’t have to waste time in the cash/credit card line. (They were seriously 30 cars deep this weekend and Neal and I were so thankful we could zip through!)

Best Day & Weekend Getaways from Chicago

How does Zipcar differ from Car 2 Go?

Car 2 Go just launched in Chicago. So you may be wondering how this differs from Zipcar and which one is for you. Essentially, it’s another cool car share company, and both it and Zipcar definitely have something to offer!

The biggest difference is that Car 2 Go is basically like those Lime Bikes or Birdies scooters you see in other cities. You see one, check it out, drive it, and then you can leave it parked on the street wherever you want (as long as it’s approved in the neighborhood, it sounds like they have some restrictions on that). They offer three kinds of vehicles–Smart cars, and two types of Mercedes.

There are a couple of cons with Car 2 Go though that you don’t get with Zipcar.

First, is that the car isn’t yours while you aren’t in it. So if you take it to the grocery store, you could come back out and have it be gone with an arm full of groceries. Also, you can only park it on the street where there isn’t a residential permit required. Which is tricky a lot of places in the city. Also they are prohibited in certain neighborhoods all together. I believe Lincoln Park, East Lakeview, and Wrigleyville are among them.

So, essentially, Car 2 Go is really handy in specific instances (if you live in a specific neighborhood and only want to drive one-way, to another neighborhood that allows them), but Zipcar definitely gives you a lot more options whether you’re running errands, commuting, and especially for taking a trip out of the city for a day or weekend getaway!

Jess Keys of the Golden Girl Blog Weekend Getaway With Zipcar

What are your favorite day or weekend trips to get out of the city? Please share below so we can all check them out! 

Thanks to Zipcar, a company we love, for sponsoring this post! This post has been updated periodically to reflect the new places we’ve visited and loved, and still stand behind Zipcar as a great car rental option many years later! 

Remember, if you’re interested in signing up for Zipcar, if you sign up through my link you’ll get a free month trial, waived membership fee, and $25 in free driving credit!