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Otherwise known as the Windy City, Chicago is known for its plethora of restaurants, impressive retail shopping, local attractions, and vibrant nightlife. To fully take advantage of this wonderful city, here are our top recommendations for you.


Chicago is a food lover’s paradise. When thinking of Chicago and food, 3 things should come to mind; pizza, hot dogs, and Italian beef. For our veggie and vegan lovers, scroll down for our picks for you!


With so many pizza options to choose from, where to get the best deep dish pizza is often debated and rarely agreed upon. Which is your favorite?


Hot Dogs

If hot dogs are more your speed, you are in for a treat! A Chicago hot dog is topped with yellow mustard, chopped white onions, sweet pickle relish, a dill pickle spear, tomato slices, pickled sport peppers and a dash of celery salt – just remember, no ketchup!


Italian Beef

Popular since the 1930’s, Italian beef remains a Chicago favorite. Over time, there have been different variations of the classic sandwich, but one thing remains, just how delicious it is!


Vegetarian/Vegan-Friendly Options

 With a city as big as Chicago, there is literally something for everyone!

Things to Do

  1. As Chicago’s number one tourist attraction, Navy Pier has a variety of activities that include; daily cruises, art exhibits, shopping, restaurants, and the Centennial Wheel.
  2. The Chicago Cultural Center is a fan favorite for locals and visitors. With free art exhibits, building tours, and community events, plus, it is home to the world's largest stained glass Tiffany dome - you have no reason not to go.
  3. Visit Millennium Park and see the Chakaia Booker sculpture exhibit, the Lurie Garden, and of course, Cloud Gate, or more commonly known as “The Bean.”
  4. If you are looking for a picture worthy shot, here it is! Buckingham Fountain, located in the center of Grant Park, is a Chicago landmark and one of the largest fountains in the world.
  5. For art lovers, the Art Institute of Chicago has the largest collection of Impressionist paintings outside of Paris – wow!
  6. Learn about the history and architecture of the buildings along the Chicago River during a Chicago Architecture Foundation River Cruise, a must-do for out-of-towners.
  7. Ultimate Museum Experience – All within walking distance from one another on Museum Campus (a scenic walkway along Lake Michigan), you will find the Field Museum, the Shedd Aquarium, and the Adler Planetarium.
  8. If you are interested in learning how Chicago came to be, which of your favorite childhood toys originated from Chicago (i.e. Lincoln Logs!), and what “really” happened during The Great Chicago Fire of 1871, then look no further than the Chicago History Museum.
  9. See Chicago from new heights! Check out the views from the Willis Tower Sky Deck or visit the 360 CHICAGO Observation Deck, formerly known as the John Hancock Observatory to fully experience the beauty of the Chicago skyline.
  10. A tranquil escape can be found at the Garfield Park Conservatory. Constructed in the early 1900’s, the Garfield Park Conservatory is one of the largest greenhouse conservatories in the United States – a gem worth visiting.


Not for the faint-hearted, Chicago gives “retail therapy” a whole new meaning. Spanning over 13 blocks, and with 460 retailers, The Magnificent Mile is a shopping utopia. If that doesn’t satisfy your shopping palate, you can explore the stores inside the 900 North Michigan Shops or visit Water Tower Place. If you are still hungry for more shopping, visit Block 37, the newest downtown Chicago shopping experience and destination. 



If music is on your mind, Chicago is where you want to be! If you’re in the mood for the blues, you’ll want to go to Buddy Guy's Legends, Blue Chicago, or Kingston Mines. If Jazz is more your style, try your luck at the Green Mill (depending on the night of the week), Jazz Showcase or M Lounge.

If your heart is set on comedy, Chicago is home to The Second City. Notable Second City alumni include; Steve Carell, Tina Fey, Chris Farley, Dan Aykroyd, John Candy, Bonnie Hunt, and Jane Lynch. If you’re looking for more laugh-out-loud comedy options, there’s also UP Comedy Club and Zanies Chicago.

For something different, the Chicago Athletic Association takes you back in time. With an impressive game room that offers billiards tables, a full-sized bocce court, cards, checkers and chess tables, foosball, shuffleboard, and a rooftop restaurant with terrace, the scenic views of Millennium Park, the Art Institute of Chicago and Lake Michigan are ideal.