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Chicago Travel Guide: Attractions, Things to Do & Tickets
Discover the best attractions, tours, and experiences in Chicago, United States. Book tickets online on HolidaySG.
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Govt fee: ETA: US$40 · B1/B2 Visitor Visa: USD 185 · ESTA: USD 40.00 · HolidaySG assistance: S$65
Top things to do in Chicago
See all 101-day tour of Chicago, USA Day Tours
Art Institute of Chicago Private Expert Guided Tour Day Tours
Best of Chicago full-day tour
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Chicago City Minibus Tour Day Tours
Chicago City Tour with Architecture River Cruise Option Day Tours
Best areas to visit in Chicago
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Top attractions in Chicago
See all 10American Writers Museum
American Writers Museum: Entry Ticket
Chicago Architecture Center
Chicago History Museum
Chicago History Museum: Entry Ticket
Columbus, OH: Columbus Zoo and Aquarium Entry Ticket
Compare top attractions in Chicago
| Attraction | From | Time to allow |
|---|---|---|
| American Writers Museum | SGD 13.47 | 2 to 3 hours |
| American Writers Museum: Entry Ticket | SGD 12.79 | 2-3 hours |
| Chicago Architecture Center | SGD 18.00 | 90 minutes |
| Chicago History Museum | SGD 22.00 | 2-3 hours |
| Chicago History Museum: Entry Ticket | SGD 21.73 | 2-3 hours |
| Columbus, OH: Columbus Zoo and Aquarium Entry Ticket | SGD 37.16 | Full day |
Prices are HolidaySG "from" prices and can change with date and ticket type; check the product page before booking.
Transport in Chicago
See all 10Useful links for Chicago
Chicago travel FAQs
Questions about booking, payment, tickets or cancellations? See our Help Centre.
Discover popular attractions and experiences in Chicago, United States on HolidaySG. Browse our curated selection above to find the best things to do, from sightseeing tours to family-friendly activities.
While not mandatory for most activities, we recommend travel insurance for international trips. It provides coverage for trip cancellations, medical emergencies, and lost belongings.
Check out other destinations in United States on our platform. We have activities across multiple cities to help you plan a comprehensive trip across United States.
Check our Transport section above for airport transfers, city passes, and public transport cards available in Chicago. Pre-booking transport saves time and often money.
Yes! We offer a variety of guided tours in Chicago including walking tours, food tours, cultural experiences, and day trips to nearby attractions. Browse the 'Things to Do' section above.
The best area depends on your interests — whether you prefer being near major attractions, nightlife, or cultural sites. Browse our Chicago activity listings to see which areas have the most to offer.
Yes! Check our E-SIM section above for digital SIM (eSIM) options. eSIMs can be activated before you arrive, giving you data connectivity as soon as you land in Chicago.