Chicago is a traveler’s paradise! The windy city is internationally praised for its distinctive cuisine (deep-dish, anyone?!), appealing architecture, bustling nightlife, and sports superfans. With so much to offer, a trip to Chicago can easily end up being a whirlwind of restaurants, bars, sights, sounds, and activities. We’ve put together this handy Chicago travel guide so you don’t miss any of the city’s must-dos.
What to Eat
If you’re traveling to Chicago for a couple of days, we recommend waking up with chicken and waffles, the perfect bridge between breakfast and lunch. Chicago has some excellent restaurants with their own take on this classic Southern dish:
- Luella’s Southern Kitchen | 4609 N Lincoln Ave, Chicago IL 60625
- Jam | 2853 N Kedzie Ave, Chicago IL 60618
- Batter & Berries | 2748 N Lincoln Ave, Chicago IL 60614
You can’t travel to Chicago without stopping at a deep dish pizza restaurant. Any of our top Chicago pizza places will keep you dreaming of Chicago long after your trip is over.
Head over to the West Loop for dinner. While there are tons of trendy and delicious spots on this side of town, we’re huge fans of these 14 restaurants:
- The Publican | 837 W Fulton Market, Chicago, IL 60607
- Mad Social | 1140 W Madison St, Chicago, IL 60607
- Leña Brava | 900 W Randolph St, Chicago, IL 60607
What to Drink
Calling all tequila lovers and adventurous drinkers. If you’re searching for tequila bars to visit while you’re traveling to Chicago, we recommend visiting these establishments to sip on delicious top-shelf tequilas from around the world.
- D.S. Tequila Company | 3352 N Halsted St, Chicago, IL 60657
- Del Toro | 2133 S Halsted St, Chicago, IL 60608
- Blue Agave Tequila Bar & Restaurant | 1050 N State St, Chicago, IL 60610
Stay cool in the hot Chicago summer with a frozen drink! You can find plenty of boozy (and virgin) slushy goodness at these 10 bars:
- BomboBar | 832 W Randolph St, Chicago, IL 60607
- Shore Club | 1603 N Lakeshore Dr, Chicago, IL 60610
- The Bird Cage | 5310 N Clark St, Chicago IL 60640
Many people travel to Chicago to view the beautiful skyline that is visible from these rooftop bars:
- Offshore | 1000 East Grand, Chicago, IL 60611
- LondonHouse Chicago | 85 East Wacker Drive, Chicago, IL 60601
- Fountainhead | 1966 West Montrose Avenue, Chicago, IL 60613
What to See
Spend a day sightseeing, walking, or biking the length of the Chicago Riverwalk. You can see live music, observe the river, shop, boat, and swim in this multi-use Chicago attraction. Must-sees at the Riverwalk include:
- Island Party Hut | 355 Chicago Riverwalk, Chicago, IL 60601
- The Jetty | Chicago Riverwalk, Chicago, IL 60606
- The Riverwalk Gateway | beneath the Lake Shore Drive Bridge
Observe great art, animals, and historical artifacts at these iconic Chicago museums.
- Shedd Aquarium | 1200 S Lake Shore Dr, Chicago, IL 60605
- Frederick C. Robie House | 5757 S Woodlawn Ave, Chicago, IL 60637
- Field Museum | 1400 S Lake Shore Dr, Chicago, IL 60605
What to Do
Fans of off-the-beaten-path movies and supporting local businesses will love taking in a show at one of Chicago’s indie movie theaters.
- Music Box Theatre | Southport Ave, Chicago, IL 60613
- The Glen Art Theatre | 540 Crescent Blvd, Glen Ellyn IL, 60137
- Pickwick Theatre | 5 S Prospect Ave, Park Ridge, IL 60068
Those traveling with teens, or have youthful energy to spare, will love these 10 fun Chicago attractions:
- Maggie Daley Park | 337 E Randolph St, Chicago, IL 60601
- Navy Pier | 600 E Grand Ave, Chicago, IL 60611
- 360Chicago | 875 N Michigan Ave 94th floor, Chicago, IL 60611
You might also like to indulge in some Mary Jane while you’re traveling to Chicago since it was legalized recreationally in January! Shop Chicago’s largest dispensary in River North. Here are a few more recreational marijuana dispensaries in the area:
- Dispensary 33 | 5001 N Clark St, Chicago, IL 60640
- Windy City Cannabis | 923 W Weed St, Chicago, IL 60642
- Sunnyside | 436 N Clark St, Chicago, IL 60654
At UrbanMatter, U Matter. And we think this matters.
Tell us what you think matters in your neighborhood and what we should write about next in the comments below!
Featured Image Credit: Navy Pier