Downtown Holidays
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Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was S$908, price is now S$611 per person
S$611
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
The staff was incredible, they went out of their way to assist and resolve immediately with any issues we had. Marina, Terina, Gazelle, Nicky and the engineer were all great, incuding the cleaning staff. Breakfast and coffee and fruit were fantastic. Will definitely recommend to family and friends and visit again, if we come into the city.
Reviewed on 28 Jun, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was S$1,152, price is now S$820 per person
S$820
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Clean room and staff was great.
Reviewed on 28 Jun, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was S$1,862, price is now S$1,331 per person
S$1,331
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
The Trump hotel is always impeccable and this time was no different. We did bring our newborn (first time parents) and they were beyond accommodating; they provided us a crib.
Reviewed on 28 Jun, 2026
Kinzie Hotel
Downtown Chicago
Price was S$995, price is now S$745 per person
S$745
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (2,134 reviews)
Room is clean and well appointed. Staff are friendly and helpful. Complimentary happy hour and breakfast are bonus. Above all, the location of this boutique hotel is central and convenient for food and walking to the river front.
Reviewed on 28 Jun, 2026
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Price was S$987, price is now S$749 per person
S$749
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (2,047 reviews)
It was an ok stay. Room was clean and the hotel was close to the sites/museums we wanted to see.
Reviewed on 26 Jun, 2026
Where to stay in Downtown
Find the best Downtown areas and neighborhoods for the activities you enjoy most. Learn more about Downtown
North Side
1 out of top 10 points of interest in this area
While visiting North Side, you might make a stop by sights like Michigan Maritime Museum and North Beach.
Top hotels in Downtown
Historic Hotel Nichols
201 Center St South Haven MI
The price is S$417 per night from 12 Jul to 13 Jul
S$417
12 Jul - 13 Jul
includes taxes & fees
9.6/10 Exceptional! (167 reviews)
"My two cousins and I recently stayed the weekend at this Historic Hotel. We loved our stay. The hotel is awesomely historic and unique with comfortable room and beds, gracious friendly staff, super happy hour with drinks and charcuterie, delicious breakfast each morning, great location within walking ..."
Reviewed on 23 Jun, 2026
Old Harbor Inn
515 Williams Street South Haven MI
Fully refundable
The price is S$283 per night from 1 Jul to 2 Jul
S$283
1 Jul - 2 Jul
includes taxes & fees
9.6/10 Exceptional! (749 reviews)
"A nice walkable location near waterfront amenities shops restaurants A friendly town with no pretense!"
Reviewed on 20 Jun, 2026
Best Western Plaza Hotel Saugatuck
3457 Blue Star Highway Saugatuck MI
The price is S$184 per night from 6 Jul to 7 Jul
S$184
6 Jul - 7 Jul
includes taxes & fees
8.2/10 Very good! (1,003 reviews)
"Everything was good, convenient parking, clean room"
Reviewed on 28 Jun, 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.
Stay near popular Downtown attractions
* 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.