Top 50 Best Things to Do in Chicago
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Top 50 Best Things to Do in Chicago

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  • The Art Institute of Chicagotop_1

    The Art Institute of Chicago
    󰺂8.3

    31.66
    Chicago,Grant Park639m from downtown
    :
    Lake views from floor-to-ceiling windows in the modern wing
    󱨜Admire 5,000 years of art treasures
    󱨠Saved by 311 person󱨠262 positive reviews
    4.7/5
  • 360 CHICAGOtop_2

    360 CHICAGO
    󰺂7.7

    23.75
    Chicago,Downtown Chicago2.4 km from downtown
    :
    󰀆Watch the fireworks spectacular every Wednesday and Saturday night
    View city from 1350 ft glass
    󱨠Saved by 181 person󱨠98% positive reviews
    4.8/5
  • 875 North Michigan Avenuetop_3

    875 North Michigan Avenue
    󰺂7.7

    23.75
    Chicago,Downtown Chicago2.4 km from downtown
    trip best small logoNo. 1 of Night Attractions in Chicago
    :
    󰀆Enjoy Chicago night views from the 96th-floor cocktail lounge
    Panoramic view of 4 states from the 94th floor observation deck
    󱨠121 positive reviews
    4.5/5
  • Grant Park
    4

    Grant Park
    󰺂7.4

    Chicago,Grant Park944m from downtown
    trip best small logoNo. 1 of Spring Outings in Chicago
    :
    Must-visit attractions at the science complex
    󱨜Treasures of The Art Institute of Chicago
    󱨠Saved by 101 person󱨠37% positive reviews
    4.4/5
  • Field Museum
    5
    2025

    Field Museum
    󰺂7.3

    22.95
    Chicago,Near South Side1.7 km from downtown
    :
    Compound Eye Insect Underground Adventure
    󱨜Experience the awe of prehistoric giants up close
    󱨠Saved by 166 person󱨠253 positive reviews
    4.7/5
  • Rte 66
    6

    Rte 66
    󰺂6.8

    Anaheim,Anaheim City Center>100 km from downtown
    trip best TravelHotspot logoSouthern California Vintage Car River Festival Begins
    trip best small logoNo. 3 of Night Attractions in Chicago
    :
    Experience the world of Cars at a filming location
    󱨜Photograph vintage street signs and neon signs
    󱨠Saved by 211 person󱨠31% positive reviews
    4.8/5
  • Willis Tower
    7

    Willis Tower
    󰺂6.3

    36.07
    Chicago,Downtown Chicago513m from downtown
    trip best small logoNo. 4 of Night Attractions in Chicago
    :
    Challenge your courage at the Glass Observation Deck.
    󱨜Tallest building in Chicago
    󱨠Saved by 189 person󱨠238 positive reviews
    4.4/5
  • Navy Pier
    8

    Navy Pier
    󰺂6.2

    Chicago,Near North Side2.6 km from downtown
    trip best small logoNo. 1 of Family-friendly Attractions in Chicago
    :
    Sightseeing cruise on Lake Michigan
    󱨜Overlook the Chicago skyline from a Ferris wheel
    󱨠Saved by 197 person󱨠28% positive reviews
    4.5/5
  • Skydeck Chicago
    9
    2026

    Skydeck Chicago
    󰺂6.2

    36.07
    Chicago,Downtown Chicago513m from downtown
    :
    Spectacular 4-state view from the 103rd floor
    󱨜Landmark building with a black curtain wall design
    󱨠Saved by 115 person󱨠45% positive reviews
    4.8/5
  • Shoreline Sightseeing
    10

    Shoreline Sightseeing
    󰺂6.1

    39.58
    Chicago,Downtown Chicago1.4 km from downtown
    :
    Chicago River architecture boat tour
    󱨜Get an up-close view of the Chicago skyline
    4.5/5

Best things to do in Chicago (2026)

Looking for the ultimate experiences in Chicago? From iconic landmarks to hidden gems, Chicago offers an exceptional collection of activities and attractions that cater to every type of traveler.

Whether you’re here for sightseeing, adventure, or cultural exploration, these top-rated activities promise unforgettable memories.

Top-rated things to do in Chicago

If you want to make the most of your trip, these activities deliver the full Chicago experience. Expect popular attractions, unique local experiences, and must-see spots that capture the essence of the city.

The Art Institute of Chicago

• Chicago.Grant Park | 639m from downtown

• : Lake views from floor-to-ceiling windows in the modern wing,Admire 5,000 years of art treasures

360 CHICAGO

• Chicago.Downtown Chicago | 2.4 km from downtown

• : Watch the fireworks spectacular every Wednesday and Saturday night,View city from 1350 ft glass

875 North Michigan Avenue

• Chicago.Downtown Chicago | 2.4 km from downtown

• : Enjoy Chicago night views from the 96th-floor cocktail lounge,Panoramic view of 4 states from the 94th floor observation deck

Things to do for unique experiences

These activities provide memorable experiences beyond the ordinary. Enjoy cultural tours, adventure sports, guided excursions, and immersive local experiences designed for all interests.

Things to do near Chicago

If you want to explore attractions just outside Chicago, there are plenty of activities that combine scenic surroundings with convenient access to the city, perfect for day trips or short excursions.

Each of these activities offers a unique escape within 1–3 hours of Chicago, ideal for travelers who want to combine sightseeing with local experiences.

What makes things to do in Chicago special

• Iconic landmarks: Visit must-see sights that define the city.
• Local experiences: Engage in culture, crafts, and unique activities.
• Accessible adventures: Easily reachable attractions for all travelers.
• Diverse options: From relaxing experiences to adventurous outings.

Tips for booking things to do in Chicago

1. Plan ahead for popular attractions to avoid long queues.
2. Book early for guided tours or seasonal events.
3. Compare prices and packages on Trip.com for exclusive deals and bundled experiences.
4. Consider weekday visits for a quieter and more personalized experience.

Experience the best things to do in Chicago

Ready to explore the best of Chicago? Discover Trip.Best's curated list of things to do and experience adventure, culture, and unforgettable memories.

Book your perfect activities on Trip.com today, where excitement and discovery awaits.

What are the best things to do in Chicago?
The best things to do in Chicago include: The Art Institute of Chicago | 360 CHICAGO | 875 North Michigan Avenue | Grant Park | Field Museum. These activities offer a mix of cultural experiences, sightseeing, and entertainment suitable for all types of travelers.
How much do the top attractions in Chicago cost?
The Art Institute of Chicago:From €31.66 | 360 CHICAGO:From €23.75 | 875 North Michigan Avenue:From €23.75 | Grant Park:Free | Field Museum:From €22.95
What amenities or facilities can I expect at top attractions in Chicago?
Most attractions in Chicago provide facilities such as visitor centers, guided tours, parking, rest areas, dining options, and accessibility features to ensure a comfortable experience.

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