Crestwood Holidays
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Crestwood Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was S$2,188, price is now S$1,835 per person
S$1,835
per person
4 May - 9 May
found 1 hour ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.2/10 Very Good! (2,575 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on 4 Mar, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was S$3,103, price is now S$2,187 per person
S$2,187
per person
4 May - 9 May
found 1 hour ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great stay! No complaints! Breakfast buffet was a great plus!
Reviewed on 15 Mar, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was S$3,823, price is now S$3,038 per person
S$3,038
per person
4 May - 9 May
found 1 hour ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,844 reviews)
Room was perfect/staff was great
Reviewed on 12 Mar, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was S$2,445, price is now S$2,061 per person
S$2,061
per person
4 May - 9 May
found 1 hour ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Staff were great! The room units for air and heat were doing their own thing, once the heat stopped blowing it was freezing in the room and the shower leaked on the bathroom floor. Had to use lots of towels everyday.
Reviewed on 15 Mar, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was S$2,498, price is now S$2,111 per person
S$2,111
per person
4 May - 9 May
found 1 hour ago
Return direct 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
Top hotels in Crestwood
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$216 per night from 16 Apr to 17 Apr
S$216
16 Apr - 17 Apr
includes taxes & fees
8/10 Very Good! (9,944 reviews)
Very cool place to stay if you enjoy historic buildings. I would definitely stay here again. Clean room, walking distance to many places.
Reviewed on 16 Mar, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$235 per night from 22 Mar to 23 Mar
S$235
22 Mar - 23 Mar
includes taxes & fees
9.4/10 Exceptional! (3,539 reviews)
Great stay! No complaints! Breakfast buffet was a great plus!
Reviewed on 15 Mar, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$196 per night from 23 Mar to 24 Mar
S$196
23 Mar - 24 Mar
includes taxes & fees
8.6/10 Excellent! (5,746 reviews)
Yes great
Reviewed on 15 Mar, 2026
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.
Popular places to visit
Wrigley Field
Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.
McCormick Place
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Millennium Park
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
What to do in Crestwood
Skydeck - Willis Tower Admission
S$56
per adult
98% of travellers recommend
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* 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.
