Chicago is an iconic American city; I don’t need to tell you that. But as I discovered during my first trip to the Windy City, there’s a lot more to Chicago than its famous landmarks and deep dish pizza.
I spent 3 days eating, drinking, and biking my way through the city with the help of my friend (and Chicago native) Kevin. Based on that experience, I’ve put together the following list of my favorite places to eat, drink, and see in this fantastic lakeside city.
Where to Eat
- Portillo’s – A classic Chicago restaurant for the Italian beef sandwich. It’s touristy, but still worth a visit for the quirky atmosphere.
- Redhot Ranch – This is one of our top recommendations for a Chicago-style hot dog and fries. Cheap and delicious.
- Gene & Jude’s – If you’re venturing out of the city proper, this is another spot worth visiting for a hot dog.
- Lou Malnati’s – An iconic spot for deep dish pizza, though be aware that the choice of deep dish restaurant is a very personal, divisive matter for many Chicagoans.
- Giordano’s Pizza – The other famous deep dish place in Chicago (along with Lou Malnati’s). If you love deep dish, you should probably try both to be thorough. :)
- Pequod’s Pizza – More of a locals’ spot for deep dish pizza, great if you want deep dish without the tourist crowds.
- Gino’s East – Another big name for deep dish that’s worth a visit.
- Pizano’s – A charming, old-school Italian place for deep dish pizza and other staples.
- Vito & Nick’s – If you want to try the distinctive South Side Chicago style of thin crust pizza, this is the place.
- Girl and the Goat – An upscale, hip small plates restaurant from a Top Chef winner.
- Au Cheval – A hipster bar and diner known for its burger.
- The Bad Apple – Good burgers and great cheese curds (saving you the drive up to Milwaukee).
- Longman & Eagle – An unassuming, Michelin-star restaurant. Plus, there are many places nearby to get a drink after dinner.
- The Purple Pig – A tapas-style restaurant that’s really fun with a big group. Very meat-heavy, so probably not worth it if you’re vegetarian or vegan.
- Parson’s Chicken and Fish – A fried chicken restaurant serving craft cocktails and beer. Kevin recommends sitting outside in the summer.
- The Publican – A German beer hall-style restaurant that focuses on pork and oysters.
Where to Drink
- Revolution Brewing – The largest independent craft brewery in Illinois.
- Haymarket Brewing – A cool place to watch a game and eat decent food, but the beer is so-so.
- DryHop Brewers – A neat spot with good beer.
- Half Acre Brewing – Really good beer all-around, plus a fun atmosphere. Probably Trav’s favorite Chicago brewery.
- Lagunitas Brewing Company – Getting to the brewery is a bit of a hike (it’s on the South Side), but it’s worth it for the tour.
- Piece Brewery and Pizzeria – A sports bar atmosphere with tasty New Haven-style pizza and good beer.
- Pipeworks – Another brewery that Kevin recommends. Get the double IPA.
- Twisted Spoke – One of Kevin’s favorite casual places to grab a drink.
- Map Room – One of the classic craft beer bars in Chicago.
- The Green Mill Jazz Lounge – A classic Chicago bar that dates back to Prohibition. Worth it for the history and ambiance, though don’t expect fantastic drinks or service.
- Scofflaw – This cocktail bar is a must-visit for gin lovers.
- The Signature Lounge – Located on the 96th floor of 875 North Michigan Avenue, this is a great place to take in views of Chicago while enjoying a cocktail. A much better price (and view) than the Willis Tower.
- The London House – The rooftop bar of this hotel has great lake and city views.
Chicago Activities
- Rent a bike – In addition to being a great way to get around Chicago, it’s a fun way to experience the city.
- Bike along the lakefront – The trail that runs along the lakefront offers gorgeous views. And in the summer, you can hop in the lake to cool off after a ride.
- Bike or hike The 606 – This former rail line has been converted into an elevated bike and walking path. It cuts through 3 different Chicago neighborhoods, and it’s a great way to work off all that delicious food. :)
- Take an architecture boat tour – This 1.5-hour tour is touristy, sure, but still worth it if you’re interested in history, architecture, or city planning.
- Go to a Cubs game at Wrigley Field – Whether you’re a sports fan or not, you can have a good time taking in a game at this historic stadium.
- Millennium Park – This massive, lakefront park has an endless number of activities to do. All summer long, the park hosts free movies, concerts, festivals, and more.
- Cloud Gate – Colloquially known as “The Bean,” this sculpture is the centerpiece of Millennium Park and worth visiting to get that iconic Chicago photo (though expect lots of other tourists to be doing the same).
- The Art Institute of Chicago – If you’re a fan of Impressionist art, this museum has a sizable collection (plus art of every other style imaginable).
- The Second City – This comedy club is legendary for producing the next big TV and movie stars. It’s worth seeing a show here even if you aren’t normally a live comedy fan.
- Time Out Chicago – This website is one of the best resources for finding free activities and events in Chicago.
Destination Map
Want to see all of my favorite Chicago destinations on a map that you can access from your phone? I’ve pinned each location mentioned in this guide on the Google Map below:
Final Thoughts
Three days in Chicago wasn’t even close to enough time to see all this city has to offer. I hope this guide has given you some ideas for planning your Chicago adventure, and I’m excited to see what you discover!
If you’re traveling to Chicago, I HIGHLY recommend getting travel insurance. I’ve used World Nomads since 2013 and love it. Click here to get World Nomads travel insurance – don’t leave home without it!
Prefer listening to reading? Check out the accompanying podcast episodes.
