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Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was S$3,187, price is now S$2,412 per person
S$2,412
per person
29 May - 31 May
found 15 hours ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel
Reviewed on 10 Mar, 2026
Arlo Chicago
Downtown Chicago
Price was S$2,970, price is now S$2,593 per person
S$2,593
per person
29 May - 31 May
found 15 hours ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,993 reviews)
Friendly staff, very helpful and approachable. The rooms were clean and I pay attention to these things, the room was immaculate upon checkin. I appreciated the lovely in-room espresso machine too. Good breakfast from the onsite restaurant. There’s also coffee, donuts and bubble tea cafes right across Michigan ave. Close to the art institute, the orange and red lines, and more I am sure. Highly recommend the Arlo for your stay in downtown Chicago.
Reviewed on 9 Mar, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was S$2,896, price is now S$2,583 per person
S$2,583
per person
29 May - 31 May
found 15 hours ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on 9 Mar, 2026
Tours & day trips
See all 192 activities
Flyover in Chicago
Activity duration is 30 minutes
9.8 out of 10 with 14 reviews
Free cancellation available
Private & custom tours
See all 60 activities
Chicago Cocktail Adventure Part 1
Activity duration is 3 hours
Free cancellation available
Food, drink & nightlife
See all 23 activities
Chicago's Chinatown Food and Walking Tour
Activity duration is 3 hours
10.0 out of 10 with 263 reviews
Free cancellation available
Classes & workshops
See all 21 activities
BYOB Spray Paint and Sip at Studio W.I.P.
Activity duration is 1 hour and 30 minutes
9.8 out of 10 with 235 reviews
Free cancellation available
Attractions
See all 20 activities
360 CHICAGO Observation Deck
Activity duration is 2 hours
8.6 out of 10 with 700 reviews
Free cancellation available
Top Roosevelt University Hotel Deals
Check availability on hotels close to Roosevelt University
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Hilton Chicago
720 S Michigan Ave Chicago IL
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
The Blackstone, Autograph Collection
636 S Michigan Ave Chicago IL
Hyatt Centric The Loop Chicago
100 W. Monroe St Chicago IL
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
500 South Dearborn Street Chicago IL
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.