Wondering what to do in Chicago while you’re there? Check out these Things To Do in Chicago for a Weekend Trip! Get the inside scoop on the best things to do, see, and eat in Chicago. A true Texans guide to Chicago.
Shoutout to all the wonderful recommendations from followers & friends, you guys were incredibly helpful putting this together and I never would have known about some of these gems if it weren’t for y’all. Also shoutout to the bae, who thinks he is “from” Chicago because he lived there for like…5 minutes. You were helpful too, hun.
SEE MORE : How To Travel Like the Travel Blogger on Points
Stay Alfred
WHERE TO STAY IN CHICAGO
Stay Alfred
One of the coolest kinds of vacation rentals! Basically, they buy out apartments downtown in the city and then use them as vacation rentals. Like an AirBnb, but the company itself owns these instead of another person. I can’t recommend enough, and use my code STAYLOCAL for 10% off!
Thompson Chicago
Our friends stayed up here and had an amazing experience! It was a little pricy and a little far north for our taste, but the room they were in and the views were unbeatable. If you’re a luxury-lover and don’t mind ubering around, then we highly recommend the Thompson.
Wyndham Chicago
Throwing this on this list because it was where the wedding was held! The hotel itself is gorgeous, the location is prime, and their penthouse views blew us away. If you want an unforgettable hotel, this is the place to stay.
Getting Around Chicago
While the L train is a great way to get around Chicago, the Uber and Lyft options are wonderful as well! If you haven’t taken either before, you can useTHIS promo code for a free Lyft and THIS promo code for a free Uber around Chicago!
Field Museum Chicago 
Neighborhood by Lincoln Park 
Seadogs Architecture Tour 
Art Museum
THINGS TO DO IN CHICAGO
Architecture Tour
We heard from EVERYONE that the Architecture Tour was a must-do in Chicago, so we did! We decided to go with Sea Dogs and had a great time! Got to see some incredible Chicago architecture and hear the stories behind the buildings. It was well worth the 1.5 hours and $40 and we recommend it to anyone that visits Chicago.
We recommend Sea Dogs Architecture Tour – we specifically loved our guide Maui!!!
Attend a Second City Comedy Show
One of my favorite things ever!!!! Second City is FAMOUS for being one of the best in the country, and it totally exceeded my expectations. The sketch comedy and improv were both hilarious, and I would recommend it.
Art Institute of Chicago
Disclaimer: I am not a huge museum person, so we were the only people in the group that did not go to this museum. However, our friends loved the museum and agreed it was up there with the Met! Tons of famous pieces you’re sure to recognize. Art lovers, go!
Field Museum
Much more my speed, so we headed here instead. We spent about two hours in the evolution exhibit and had a great time! If you’ve got smaller children, this would be a great place for them to spend an afternoon. Also, home to the largest T-Rex!
Skydeck Chicago 
Chicago Bean
Millennium Park & The Beach
I totally see why the bean is so famous now. We spent a solid hour taking photos with it and walking around Millennium Park. Worth a stop, even if it’s packed with tourists!
Willis Tower Skydeck
We headed there first thing in the morning because we heard lines were shorter when it opened! It was only about 45 minutes of waiting but the skydeck was pretty neat! Gorgeous views of the city and we loved getting to do the glass box.
However, we did not know that there are separate lines up top for the boxes. Expect another 10 minutes waiting and you do not get much time to take cool photos since they are shuffling you through so fast. We aren’t totally sure this was worth it, but still an experience!
Navy Pier
While I would not normally recommend this because it is crazy touristy, I will say the fireworks at Saturday night would be worth checking out! Probably a good idea to head to a rooftop bar to catch them though (some below!)
Walk (and shop) the Magnificent Mile
We started out by Millenium Park and walked quite a few miles all the way up the Magnificent Mile to Lincoln park! If you’re big fans of walking a city, I would absolutely say this is the way to go. It starts off Downtown in all the buildings, moves through the Magnificent Mile stores, hits the gorgeous little neighborhoods, and finishes off at the beach where you can chill after walking your butt off!
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Girl and the Goat 
Deep Dish Pizza 
S K Y Chicago
WHERE TO EAT IN CHICAGO
Get Deep Dish Pizza ($$)
We heard that you had to go to either Giordano’s or Lou Malnati for some famous Chicago deep dish, so we did! However, I would say Pequods is probably your best bet for a less chain-y deep dish pizza.
S.K.Y ($$$)
Okay SO not only was the food AMAZING, but we loved that this restaurant was BYOB on Sunday! We saved so much money by bringing our own bottles of wine, and that way we could spend on food we really wanted. Also, mind-blown by the food and the incredible staff at this restaurant!
The Publican ($$$$)
Oh boy, it is a splurge. HOWEVER. It was absolutely delicious and we both were surprised by how much food we consumed. If you’re foodie people, then I would put this on your list but definitely make sure you make reservations ASAP.
Girl & The Goat ($$$)
I’ve tried to get reservations here every time, and have yet to be successful. So while I can’t personally attest to the food, apparently everyone in the world loves it because god forbid I ever get in!
Hampton Social ($$)
You’ve probably seen this beauty on your instagram at some point, and for good reason! Hampton Social is a great thing to do in Chicago with your girls or bridesmaids if it’s that kind of trip. A total cutie spot you will 100% post about!
Lula Cafe ($$)
If you’re looking for a good low key brunch spot, this is the place to go. We absolutely loved our brunch here and had a great time! Plus, they’re known for having plenty of vegan and vegetarian options.
All Together Now ($$)
Adorable lunch bistro with American style food. Great if you want something fun but still casual!
Pacific Standard Time ($$$)
Another great lunch spot with delicious American food. A little on the pricier side of things, but the ratings are high for a reason!
Celeste 
Drumbar 
Beatnik
WHERE TO DRINK IN CHICAGO
Drumbar
A cozy cocktail bar with killer views of the city, perfect for you and a date!
The Violet Hour
Speakeasy style in some giant curtains, where you can pretend to be Alice in Wonderland
Beatnik
Multiple locations, and all are worth a stop by, those interiorrrrrrssss
Broken Shaker
A bar in the back of the hostel, more low key vibes but still a poppin’ spot
The Green Mill
Jazz bar and cocktail lounge, the kind of place that’s perfect if you want some live music
London House
Serving you all those rooftop views, the perfect nighttime viewing spot
Celeste
Enjoy your day cocktail in what can only be described as an English garden
The Robey
Hit the rooftop view stunning views of the Chicago skyline, or the sixth floor if you wanna chill by their pool
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