Downtown Holidays

Photo by SupremeMaster photography

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was S$1,102, price is now S$943 per person
S$943
per person
30 Jan - 1 Feb
found 9 hours ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Room was very neat and clean! Staff were very nice and helpful!

Reviewed on 30 Dec, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was S$1,539, price is now S$1,215 per person
S$1,215
per person
30 Jan - 1 Feb
found 9 hours ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great time and staff

Reviewed on 30 Dec, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was S$1,118, price is now S$987 per person
S$987
per person
30 Jan - 1 Feb
found 9 hours ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on 18 Dec, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was S$1,116, price is now S$988 per person
S$988
per person
30 Jan - 1 Feb
found 9 hours ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Everything was great!

Reviewed on 29 Dec, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was S$1,584, price is now S$1,424 per person
S$1,424
per person
30 Jan - 1 Feb
found 9 hours ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Emil was a fabulous server at the Lobby Restaurant. I think that’s his name. Tall guy. Becca at front desk also fantastic. The lady who checked us in not so good.

Reviewed on 29 Dec, 2025

Where to stay in Downtown

Find the best Downtown areas and neighborhoods for the activities you enjoy most. Learn more about Downtown
Default Image

North Side

While visiting North Side, you might make a stop by sights like North Beach and Michigan Maritime Museum.

Find hotels in North Side

Top hotels in Downtown

Historic Hotel Nichols

Historic Hotel Nichols

2 out of 5
201 Center St South Haven MI
The price is S$434 per night from 30 Jan to 31 Jan
S$434
30 Jan - 31 Jan, 2026
includes taxes & fees
9.6/10 Exceptional! (126 reviews)
Historic Hotel Nichols was a great experience for our small family. Nick (manager) was fantastic. If you are staying in town, you won't regret staying here. Location is excellent, walkable to all shops/restaurants.

Reviewed on 12 Dec, 2025

Historic Hotel Nichols
Old Harbor Inn

Old Harbor Inn

3 out of 5
515 Williams Street South Haven MI
Fully refundableReserve now, pay when you stay
The price is S$143 per night from 14 Jan to 15 Jan
S$143
14 Jan - 15 Jan, 2026
includes taxes & fees
9.4/10 Exceptional! (680 reviews)
Great location

Reviewed on 14 Dec, 2025

Old Harbor Inn
Baymont by Wyndham South Haven

Baymont by Wyndham South Haven

2.5 out of 5
1555 Phoenix Rd South Haven MI
Fully refundableReserve now, pay when you stay
The price is S$97 per night from 7 Jan to 8 Jan
S$97
7 Jan - 8 Jan, 2026
includes taxes & fees
7.6/10 Good! (1,000 reviews)
Staff was wonderful to me and my family, very family friendly, and clean!

Reviewed on 22 Dec, 2025

Baymont by Wyndham South Haven
See all 2,035 properties in Downtown
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.

* 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.