Old Town Chicago Holidays
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Top hotels in Old Town Chicago
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$283 per night from 14 Sept to 15 Sept
S$283
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,922 reviews)
"Great hotel overall. Definitely makes you feel back in time, but the bedrooms have a balance of new and old. Although a few hairs were found in the towels, despite being changed daily, I do appreciate how efficient the staff was at keeping all clean and running. Dinning is not the best, but it’s ..."
Reviewed on 15 Aug, 2025
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$293 per night from 2 Sept to 3 Sept
S$293
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,856 reviews)
"Pleasant experience. Accommodations were good. Surrounding area was convenient to shopping, eateries and p parks."
Reviewed on 13 Aug, 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$229 per night from 25 Aug to 26 Aug
S$229
25 Aug - 26 Aug
includes taxes & fees
8.4/10 Very Good! (3,681 reviews)
"Hotel was quiet. Room was comfortable. Location was great."
Reviewed on 13 Aug, 2025
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.
Things to do
Chicago By Night River & Lake Cruise
S$58
per adult
96% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
S$52
per adult
94% of travellers recommend
* 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.