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Our Chicago Staycation Itinerary

Happy Tuesday!!

I’m already counting down to the weekend–are you? I have one of the BUSIEST work weeks ahead of me that I’ve had in awhile–so I’m simultaneously excited while anxiously pulling my hair out 😛

Today I’m sharing our Chicago staycation itinerary and what we did on our anniversary weekend a couple weeks back.

To be honest, up until then, I never understood the concept of a staycation. I love my house–I love my bed. Why would I pay to stay in a hotel when I can sleep in my own bed!? (I was wrong–Neal was right–I changed my tune REAL fast!)

First, I made a movie out of the Instagram stories I posted that weekend, I thought it would make a funny recap! Keep scrolling for our full itinerary and favorite places you must put on your list for your next Chicago staycation (or vacation!)

Where to stay:

When we decided to do a staycation for our one year anniversary, the Waldorf Astoria was our first choice–it’s always been a special place for us, and we got engaged in the courtyard! (See our full engagement story with lot’s of amazing photos here!)

When we first tried to make a reservation, were very sad to find out that the hotel was fully booked, so Neal told me he’d made reservations at London House (another beautiful hotel!) but at the last minute, he was able to snag a reservation because he’s sneaky and smart ? He remembered he was a Capital One rewards member and thought to call back and ask if they had a few rooms blocked off specifically for rewards members–and they did! Just a tip to keep in mind whenever you’re booking hotels!

The Waldorf is definitely a splurge specifically reserved for special occasions–but we’ve never had such an incredible hotel experience! Even the bathrobes are far and away more luxurious than any other fancy hotel I’ve ever stayed in! (Seriously, they’re lined with this amazing microfiber blanket material that is the softest thing you’ve ever felt ? They sell them for $130 and I was SERIOUSLY considering making the investment ?). One of my favorite parts of the weekend was just sleeping in, lounging in bathrobes and watching TV!

Our friend Whitney, who works at the hotel, also REALLY hooked it up for us–she sent us champagne and upgraded our room to an amazing suite! She’s also a blogger and you should definitely give her a follow @SomethingWhitty on Instagram! Thank you for making our stay so special, Whitney!!

I've never looked more like Ed from The Lion King

I’ve never looked more like Ed from The Lion King

What to do:

Hit the spa:

Neal surprised me by booking a couple’s massage at The Waldorf’s spa! Another perk of being a hotel guest–you can access their amenities like the sauna and steam room anytime for free (amazinggg!) It was so amazing I couldn’t believe how fast 60 minutes flew by! They include aromatherapy oils with every massage and you get to smell and pick out your scent beforehand which I thought was a really nice touch.

Shop around:

One of our favorite things to do is just walk around with coffee and browse the shops along Rush street in the Gold Coast (this area is called the “Viagra Triangle” area–because it’s where all the rich old men live ? Seriously though, that’s it’s name!) and on Michigan Avenue! It’s easy to make a day of it, and is one of my favorite places to be in the fall! Meander in and out of the super high end shops like Barney’s, Hermes, but also the budget-friendly fan favorites like Madewell, J.Crew, Nordstrom are all within walking distance!

(If you happen to grab a coffee at the Starbucks on Rush, head upstairs to rest and give your feet a break by the fire! I used to live down the street and it’s where I spent about 13 hours a day working right after I quit my advertising job ?)

the Waldorf's coffee shop, Petite Margaux,

Walk along the lake: 

Grab a coffee (the Waldorf’s coffee shop, Petite Margaux, is SO CUTE) and head down to the lakefront path. This is another reason I would recommend staying in the Gold Coast–it’s so close to the lake and you’ve honestly never seen a beautiful view of the city. I always forget how breathtaking the view is–even after all these years living here, it never gets old.

Where to eat:


Butch McGuires:

Okay, you won’t find this recommendation on most lists–but if you’re like us and you love a good divey Irish bar with quality, cheap brunch–this is IT. We both frequented Butch’s a lotttt in our younger years–so it’s fun to come back (this time not at 4am ?). We came here for brunch on Saturday because it’s a quick walk from the Waldorf and it never disappoints!

Any sidewalk cafe in the Viagra Triangle:

 There are so many adorable and awesome lunch spots on Rush–they all have sidewalk cafes with bistro chairs and it’s about the closest thing you will ever get to Paris here in the midwest. You can’t go wrong–I’ve eaten at all of them and they are all great–but the best part is the people watching. Some favorites: Luxbar (they have a great hearts of palm salad), Tavern on Rush (club sandwich is awesome), Hugo’s Frog Bar, and Gibson’s.

For dinner:

[one-half-first]Our Chicago Staycation Itinerary[/one-half-first][one-half]

Our Chicago Staycation Itinerary


Le Colonial (above, left):

My favorite restaurant in Chicago! (Okay, it’s tied with Boefhaus. But they’re so different, you can’t compare!) It’s an upscale Vietnamese restaurant–but you HAVE to eat upstairs. Non negotiable. (The downstairs is fancy white tablecloth and if we’re being honest–can be very stuffy, haha!) The upstairs is homy, cozy, you can sit at the bar, at a table, or on the terrace (they enclose it in the winter and will also give you blankets!) Our favorite part are the people who work there. We inevitably end up closing down the bar and hanging out with Michael, the Maitre’D, and Alfredo, the bartender.

As for food, a couple things to not miss: Vietnamese Ravioli, Ribs, Spring Rolls, Pho, Bun, and basically anything else they tell you to order–just trust them. We’ve never had anything we didn’t love.

Bavette’s (above, right):

Neal’s favorite restaurant in Chicago. If you want steak, forget any of the traditional steakhouses–THIS is where you come. We split the ribeye and got fries and Brussels sprouts and it was the perfect amount of food. Neal says it’s the best steak in Chicago–I think it’s tied with Boefhaus–it’s tough to say 😉 But the ambiance at Bavette’s is very tough to beat. It’s incredibly dimly lit and romantic. You feel like you’re in a french speakeasy. I can’t recommend it enough.

Margaux Brasserie:

The Waldorf’s swanky (but unstuffy) restaurant and bar–it’s basically everything you want in a destination when you’re looking to dress up and go somewhere cool (but not overly trendy) to drink martinis and good wine. It’s always laid-back, the service is always great, and they have some great food too. Try the duck wings l’orange!

Where are your favorite spots for a Chicago Staycation!?