A few years back I traveled to Chicago for work. I was there for less than 24 hours and it was in the middle of winter so I basically went to the office I was visiting and we went out for dinner and drinks. There was very little sightseeing or much exploring. Which didn’t really leave me with the best impression of the city. I’m so glad I went back for another trip, especially during the summertime. Chicago is such a GORGEOUS city. All the tall buildings were reflecting the blue sky and the water and it really was a great mix of a busy city with plenty of opportunity to enjoy the outdoors. So, basically everything I want out of a city, haha. I hope to return sooner than later, and if you have any suggestions for Chicago, please share below!
Here’s 15+ places to eat, drink and have fun in Chicago!
Where to Eat
Eataly Chicago – This place is two stories of Italian food, goodies, wine and restaurants. Stop in and visit any of the restaurants within the building or pick up some wine and fancy cheese to enjoy al fresco. There are multiple restaurants in the building, but we had to try the pasta. And it was DAMN GOOD. You really can’t go wrong with fresh pasta. Mine was perfectly al dente. Next time I’d love to try the squid ink pasta. A restaurant here in Cincinnati used to have squid ink pasta on the menu and I’ve been obsessed with it since.
Au Cheval – Au Cheval is on everyone’s list for best burger in Chicago and there is good reason why. It’s mouthwatering. The burger itself is juicy and freshly made. The bun can actually withstand all the meat and – and the best part – the piece de resistance – the freshly made pickles. If, I mean when I return, I’ll inquire about ordering an entire cup of these delicious, fresh, crunchy pickles. And then eat them alongside the salty french fries. If you haven’t realized yet, this meal is a commitment. You’ve got to be prepared to wait a while for a table and be ready to EAT. Then after, you probably want to set aside some time for a stroll to work off the meal and a nap if you’re lucky. We take our burger consumption very seriously around here.
Portillo’s Hot Dogs – I knew I had to try a Chicago-style hot dog and Portillo’s was the easiest to get to. I’ll be honest, it was just OK. I totally recommend trying out the popular local cuisines, so I definitely don’t regret this meal, but next time I’ll try another hot dog place. If you’ve been to Chicago, I’d love to hear your favorite place!
Big Star Tacos – I’ve read some hit and miss reviews about this place, but I had no complaints about my experience. We dined here on a Thursday night. There wasn’t a wait, but the place was pretty packed. Luckily there is a huge patio with tons of outdoor seating. Our server was fast and accommodating and the queso was awesome. This plus margaritas was all I needed, but I added some fish tacos too. Really a great spot in Wicker Park for some outdoor dining.
Where to Drink
Untitled – If you’re looking for a fun speakeasy experience, then Untitled is definitely a place to get it. And it’s honestly great for small groups because this place is huge. When you go to the address, you’ll realize there isn’t a sign or anything outside to direct you in, but you’ll see a bouncer waiting nearby a door. You’ll walk up and actually head down a set of stairs. You’ll want to do a lap around the entire place to take it all in and then treat yourself to a cocktail. The often have live Jazz music and you’ll see plenty of people dancing, but there are also tables and seating available if you’re in the mood to chat and catch up with people.
The Drifter @ The Green Door Tavern – If you want an authentic speakeasy experience, you really can’t beat The Drifter. This place actually was a speakeasy during Prohibition. You’ll want to head to The Green Door Tavern which is a fun bar in itself. But when you’re ready for the speakeasy experience, head to the back and find the stairs that head down. At the bottom of the stairs there will be an entrance to The Drifter to your right. The Drifter only seats 37 people so you may have to wait. The drink menu changes every night and is served via tarot cards. You can also order a specific cocktail or something off the beer menu.
Where to Have Fun
Sidewalk Food Tour – The Sidewalk Food Tour company hosts food tours all over the US and the world, so you know the standards are going to be pretty high. I was really excited when I first came across the food tour because when I was planning the trip, I had such a long list of places and food to try. I knew there’d be no way I’d even make a dent in that list. Luckily, with the food tour, I was able to try the quintessential Chicago style pizza at Lou Malnati’s, a dish from Xoco (owned by Rick Bayless, a Top Chef Masters winner!) which was on my Chicago bucket list and more. Read my full review here.
Hop On Hop Off Bus – If it’s your first time in a city, I find tour buses to be really helpful in getting oriented with the layout. Plus, you’ll also hear some interesting history and other fun facts. This was our second time taking a Hop On Hop Off Bus (the other time was in NOLA) and I was once again impressed with the tour guide. In my experience, the guides have always been really enthusiastic and no guide shares the same details as the others so even if you go through the same route multiple times you’ll still get a unique experience. If you’ve never taken a Hop On Hop Off Bus, I’ll try to explain it for you. The bus follows a specific route and makes many stops at points of interest like museums, parks, venues, etc. With your ticket you can ride the bus all day and hop on it at any stop and hop off at any stop. It’s really convenient if you plan ahead and determine additional places you might want to visit near stops so you can avoid taking an uber for everything. And overall it really helps you get the lay of the land, so if possible, I suggest taking the bus on your first or second day in the city.
All the games are free!!! With the exception of two pinball machines (the Game of Thrones one and the one to the right) all the arcade games can be played for free. The drink selection was great with cocktails and a well-curated craft beer list. I personally love these kind of bars to start the night because they have great beer and some fun entertainment that’s not just focused around really loud music and crowds. Plus they had signs for an upcoming Rick & Morty-themed brunch. That’s how you immediately know this place is awesome.
Emporium Arcade Bar (in Wicker Park)
Yes, we went to two barcades in one weekend! My BF is a gamer so we always try to visit some places that appeal to his interests when traveling. I personally prefer the Beercade HQ over the Emporium Arcade Bar, because the games at the Emporium aren’t free. However, the Emporium did have live music which is always a plus in my opinion, plus there were tons of other bars and venues within walking distance so you can hop around to other places easily.
Skydeck Chicago aka Willis Tower
The Willis Tower is home to Skydeck Chicago. For the Skydeck, you’ll get to go up to the 103rd floor, watch a short film explaining the history and other interesting details about the building and then check out some aaaaamaaaazing views. Really, it’s gorgeous up there. You can potentially see 3 states at once if skies are clear. During our visit, the lake looked just gorgeous with the sun setting. And if the views aren’t enough, there are several spots where there is a glass extension or ledge from the building like an enclosed deck. You can step out and look all 103 floors (1353 feet!) down. The staff will grab your photo and you can take some shots for yourself. In my experience, I wasn’t nervous the entire time I was in line, but once I had to step out onto the deck my body did NOT want to move. I was laughing like a crazy person and was all red and could barely step out on the ledge. And I had quite the audience laughing along with or at me. It was fun and the pictures are amazing so I recommend doing your best to fight any fears of heights and check it out.
We stopped here on the Thursday night of our visit and barely waited in line. Maybe 20 minutes max. We were able to get inside the building and only hit a short queue right before where they show the short film. But, when we came by on Sunday afternoon we could see a line out the door of the building. Insane!! So, if you can, go on a weekday or get there first thing when it opens on the weekend.
It’s a must for a reason! You gotta take a bean selfie. Like any good city, Chicago hosts regular free entertainment events at Millennium park too so there’s a good chance you’ll find some free concert going on while you’re visiting. Enjoy the grounds and tunes and be sure to get plenty of photos.
We stopped here on a Saturday and there was definitely a good sized crowd but nothing unmanageable. We probably waited closer to 30 minutes to get our tickets for the Millennium Wheel and then maybe 5-10 minutes to get on the Ferris Wheel. And this isn’t your regular ferris wheel. It’s a completely enclosed seating area and the ride lasts probably 15 minutes or more. You’ll stop at plenty of parts which lets you take in the view and grab lots of photos of the GORGEOUS pier and it’s surroundings. There are other rides available that are probably better suited to children.
Architecture Tour Cruise
I loooooved this! Anytime I asked someone about what to do in Chicago, literally everyone mentioned taking an architecture cruise. And it really did exceed expectations. You’ll access the tour via the riverwalk. I enjoyed our seats near the side of the boat because I was able to move around and get photos at different angles without being in anyones way. The guides did a great job of sharing the architecture history and tying it into historical events of the city. Starting the tour I didn’t think I could be that interested in the architecture but I was quickly proven wrong.
Michigan Mile and Riverwalk
There is so much to see in Chicago and there’s a lot you can actually do by foot. I absolutely suggest not overloading your schedule for your trip and planning in time to walk through Michigan Mile and the Riverwalk. The Michigan Mile can definitely be crowded but you can hop into any stores you’d like for a bit of shopping. The Riverwalk itself is just so relaxing and you’ll pass plenty of restaurants and bars that you can hop into or relax at for a drink.
Thank you to Smart Destinations for providing me with a complimentary Go Chicago Pass. The pass included access to the Navy Pier rides, Skydeck, Hop On Hop Off Bus and the Architecture Tour. Plus, there are actually many more attractions you can visit using the Go Chicago Pass. While the pass I was provided was complimentary, all opinions are my own and I highly suggest visiting their site and seeing if the pass would be a good option for you. If you plan to check out a lot of the popular attractions it can definitely save you some money.
Pin the image below to your Pinterest board to save this article! Thanks so much!
Leave me a comment below for any other places I need to check out during my next Chicago visit! ❤️
Casey is the founder of Casey La Vie & has been running this travel and lifestyle blog since 2016. She’s on a mission to balance her career as a social media manager with exploring her home of New York City and seeing more of the world.