Top Things To Do When Visiting Chicago

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  • A list of the top activities in the Chicago Area
  • Activites include descriptions, prices and links to websites


Eat Delicious Pizza

No trip to Chicago would be complete without trying the city’s iconic deep dish pizza. There are a ton of delicious choices to choose from though the best option will vary depending on who you ask. To narrow it down, popular favorites include:

  1. Lou Malnati’s Pizzeria
  2. Giordano’s
  3. Gino’s East of Chicago

Millennium Park Map

Millennium Park - Free

A trip to Chicago isn’t complete without a visit to Millennium Park. Often referred to as Chicago’s Front Lawn, the park is located in Downtown Chicago and includes city highlights like The Bean (Cloud Gate), Jay Pritzker Pavilion, the Crown Fountain and the McCormick Tribune Plaza & Ice Rink. I recommend setting aside two hours to explore the park, although you could easily spend all day.

Skydeck Chicago - $23

Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest building in the world -- the Skydeck offers spectacular sweeping views and is full of interactive exhibits. To complete your exciting Chicago experience, head to the Ledge, a glass balcony showcasing unbeatable views of Chicago’s top attractions like Wrigley Field and the Navy Pier. With mobile tickets, simply scan your phone for direct entry into the SkyDeck.

Art Institute of Chicago - $35 (Fast Pass Admission)

Art lover or not, the Art Institute of Chicago – the second-largest art museum in America – is not to be missed. Located in Chicago’s Grant Park, this amazing museum features an extraordinary collection of Impressionist, post-Impressionist, modern and contemporary art from such masters as Monet, Renoir, van Gogh, Picasso and Pollock, as well as stunning new-age architectural, industrial and graphic design. With mobile tickets, simply scan your phone for direct entry into the Art Institute.

Free Tours by Foot - Free

A guided tour of Chicago with no upfront cost, because you get to choose what to pay based on what you feel the tour was worth. My fiancé and I have had great experiences with similar pay what you like tours in other cities, so we reserved spots for two tours in Chicago: the Lincoln Park & Gangster Tour and Loop & Millennium Park Tour. They offer multiple tours, which you can review and reserve spots for by clicking on the link below.

This type of tour is a great deal compared to other tours that require tips in addition to an up-front payment. I know there are often questions regarding how much to tip, but there is no set answer as the amount you choose to tip should be a personal choice based on your budget and experience. However, if you’d like a reference point, on a 2-Hour Tour we tip $20 per person if we enjoyed the tour and $10 per person if we feel the tour or the guide wasn’t particularly interesting, but the experience was informative.  

Chicago City Hop-on Hop-off Tour - $19

See all the sights of Chicago at your own pace! On a Chicago City Hop-on Hop-off Tour you can get off the bus at any scheduled stop to visit Chicago's most popular attractions, then pick up the tour where you left off or get on at any other regular stop on the route. For individuals and families, this is the best way to see the sites!

The tour includes the signature route which runs year round, while the seasonal neighborhoods routes and night tour operate May - September only. See itinerary below for specific stops.

Chicago CityPass - $99.75

Chicago CityPASS is the best deal in the Windy City, giving you discounted admission to five of the city's premier attractions. The Chicago CityPASS ensures you'll get the most out of your vacation - yet it is so compact it will fit into your back pocket. It's all you need to see the best of Chicago!

Chicago Odyssey Dinner Cruise - $88.26

Expect the exceptional on this 2.5-3 hour premier Chicago dinner cruise experience. Newly renovated, this luxury vessel features a newly furnished rooftop lounge, posh atmosphere and stylish interior. Relish a 3-course plated meal with celebrity-chef inspired dishes prepared from fresh ingredients right on-board. Dance the night away to DJ entertainment or simply relax in the elegant ambiance and admire unmatched views of the world-famous Chicago skyline as you glide along the shores of Lake Michigan.

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