A Complete Traveler’s Guide to Chicago: What to Eat, Drink, See & Do

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

traveler's guide chicago
Photo Credit: Luella’s Southern Kitchen


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:

traveler's guide chicago
Photo Credit: Pequod’s


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.

traveler's guide chicago
Photo Credit: Mad Social


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:


What to Drink

traveler's guide chicago
Photo Credit: Del Toro

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.

traveler's guide chicago
Photo Credit: Bombobar

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:

traveler's guide chicago
Photo Credit: Offshore

Many people travel to Chicago to view the beautiful skyline that is visible from these rooftop bars:

What to See

traveler's guide chicago
Photo Credit: Island Party Hut

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:

Photo Credit: Robie House Facebook

Observe great art, animals, and historical artifacts at these iconic Chicago museums.

What to Do

Photo Credit: Music Box Theatre

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.

Photo Credit: Navy Pier

Those traveling with teens, or have youthful energy to spare, will love these 10 fun Chicago attractions:

Photo Credit: MOCA

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:



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Featured Image Credit: Navy Pier



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