Bolingbrook Holidays
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Bolingbrook 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 12 hours 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 12 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
ALL the employees were nice, went out of their way to help and property was clean too!
Reviewed on 16 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 12 hours 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 12 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Room was extremely small and talked to front desk and they were extremely nice and upgraded the room. The room gets extremely humid which is a problem if you want to do your hair because it turns into a frizzy mess. Hallways smelled like weed the first night.
I wouldn’t recommend this hotel at all for the price I paid.
The valet guy was amazing and extremely helpful.
Reviewed on 16 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 12 hours 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 Bolingbrook
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$153 per night from 1 Apr to 2 Apr
S$153
1 Apr - 2 Apr
includes taxes & fees
8/10 Very Good! (9,945 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
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$234 per night from 1 Apr to 2 Apr
S$234
1 Apr - 2 Apr
includes taxes & fees
8.6/10 Excellent! (2,684 reviews)
Front desk staff seemed to speak to me as if I was inconveniencing their day when you work a front desk and your people coming in from out of the area, it’s important to offer a warm and welcoming tone. I did not experience that with said staff had a massive issue with parking that led to me having ...
Reviewed on 15 Mar, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$314 per night from 5 Apr to 6 Apr
S$314
5 Apr - 6 Apr
includes taxes & fees
8.4/10 Very Good! (2,227 reviews)
STAFF were excellent. Food in restaurant really delicious.
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 Bolingbrook
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.
