Winthrop Harbor Holidays
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Winthrop Harbor 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$872, price is now S$593 per person
S$593
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)
Location was excellent. Rooms were a little smaller than I'd prefer but we got by.
Reviewed on 29 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)
Beautiful hotel
Reviewed on 29 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)
Everything was great. Clean room and great staff!
Reviewed on 29 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)
No big frills, but a solid place to stay when coming to explore the city. Good location for access to the museums with good proximity to Soldier Field. Also nice to be able to walk down the street to hit up a grocery store or convenience store. Overall a good place to chill in between city adventures.
Reviewed on 29 Jun, 2026
Top hotels in Winthrop Harbor
LA VILLA MOTEL
1401 Sheridan Rd Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
The price is S$92 per night from 13 Jul to 14 Jul
S$92
13 Jul - 14 Jul
includes taxes & fees
6.8/10 (72 reviews)
"Needed a last minute place to stay, and this was clean and quiet, with attentive staff, though poorly maintained (eg old furniture stored in the hallway, bathroom exhaust did not work). The room had a huge hot tub in the corner with a wall mirror. Fantastic location, easy drive to downtown Zion and ..."
Reviewed on 20 Jun, 2026
Motel Sun Inn
301 Sheridan Road Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
The price is S$99 per night from 30 Jun to 1 Jul
S$99
30 Jun - 1 Jul
includes taxes & fees
6.8/10 (280 reviews)
"The staff were so nice! The rooms and bathroom were so clean. The building is a little older but everything was in good shape. Free WiFi use and the air conditioner worked perfectly. The price was also fair. It was 90 dollars and a 50 dollar deposit fee but you get the 50 dollars back in your account ..."
Reviewed on 25 Jun, 2026
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
The price is S$264 per night from 13 Jul to 14 Jul
S$264
13 Jul - 14 Jul
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"Everything was excellent! The only issue was that we had to wait in line to use the microwave to heat our meals. If guests are expected to stay for an extended period, it would be much more convenient to have a microwave in each room, or at least easier access to one. Overall, we had a great experience, ..."
Reviewed on 27 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 Winthrop Harbor attractions
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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.
