Illinois Centennial Memorial Column

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Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was S$3,187, price is now S$2,412 per person
S$2,412
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy.

Reviewed on 9 Mar, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was S$2,970, price is now S$2,593 per person
S$2,593
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,993 reviews)
Friendly staff, very helpful and approachable. The rooms were clean and I pay attention to these things, the room was immaculate upon checkin. I appreciated the lovely in-room espresso machine too. Good breakfast from the onsite restaurant. There’s also coffee, donuts and bubble tea cafes right across Michigan ave. Close to the art institute, the orange and red lines, and more I am sure. Highly recommend the Arlo for your stay in downtown Chicago.

Reviewed on 9 Mar, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

4.5 out of 5
Downtown Chicago
Price was S$2,896, price is now S$2,583 per person
S$2,583
per person
29 May - 31 May
found 1 hour ago
Return 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

Tours & day trips

See all 190 activities
Flyover in Chicago

Flyover in Chicago

Activity duration is 30 minutes
9.8 out of 10 with 14 reviews
Free cancellation available
Price is S$48 per adult
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Private & custom tours

See all 60 activities
Chicago Cocktail Adventure Part 1

Chicago Cocktail Adventure Part 1

Activity duration is 3 hours
Free cancellation available
Price is S$6 per adult
Chicago Cocktail Adventure Part 1Opens in new tab

Food, drink & nightlife

See all 25 activities
Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown Food and Walking Tour

Activity duration is 3 hours
10.0 out of 10 with 263 reviews
Free cancellation available
Price is S$102 per adult
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Classes & workshops

See all 22 activities
BYOB Spray Paint and Sip at Studio W.I.P.

BYOB Spray Paint and Sip at Studio W.I.P.

Activity duration is 1 hour and 30 minutes
9.8 out of 10 with 235 reviews
Free cancellation available
Price is S$57 per adult
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Attractions

See all 21 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 2 hours
8.6 out of 10 with 700 reviews
Free cancellation available
Price is S$38 per adult
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Popular places to visit

The 606

The 606

The 606 is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Take in the live music and sunsets in the area.

The 606
Path with Yellow Flowers at the Humboldt Park Lagoon

Humboldt Park

Humboldt Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed theatre scene and entertainment choices in this vibrant area.

Humboldt Park

Logan Square Farmers Market

You can enjoy retail therapy at Logan Square Farmers Market during your visit to Chicago. Experience the acclaimed theatre scene and entertainment choices in this vibrant area.

Logan Square Farmers Market

Hairpin Arts Center

Enjoy an outing to Hairpin Arts Center during your stay in Chicago.

Hairpin Arts Center

Busy Beaver Button Museum

You can spend time studying the exhibits at Busy Beaver Button Museum during your travels in Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Busy Beaver Button Museum

Kosciuszko Dog Park

Kosciuszko Dog Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Take in the live music and sunsets in the area.

Kosciuszko Dog Park

Top Illinois Centennial Memorial Column Hotel Deals

Logan Square SRO Hotel

Logan Square SRO Hotel

2 out of 5
2001 North California Avenue Chicago IL
Logan Square SRO Hotel
The Hotel at Midtown

The Hotel at Midtown

4 out of 5
2444 N. Elston Ave Chicago IL
The Hotel at Midtown
Ray's Bucktown B&B

Ray's Bucktown B&B

3.5 out of 5
2144 N. Leavitt St Chicago IL
Ray's Bucktown B&B
The Robey, Chicago, a Member of Design Hotels

The Robey, Chicago, a Member of Design Hotels

3.5 out of 5
2018 W. North Ave. Chicago IL
The Robey, Chicago, a Member of Design Hotels
Hyatt Place Chicago/Wicker Park

Hyatt Place Chicago/Wicker Park

3 out of 5
1551 West North Ave Chicago IL
Hyatt Place Chicago/Wicker Park
Chicago Avenue Inn

Chicago Avenue Inn

2 out of 5
3305 W Chicago Ave Chicago IL
Chicago Avenue Inn
STAY

STAY

2 out of 5
1415 Ashland Ave Chicago IL
STAY
Wicker Park Inn

Wicker Park Inn

3.5 out of 5
1331 N Wicker Park Ave Chicago IL
Wicker Park Inn
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Embassy Suites by Hilton Chicago Downtown River North
See all 4,362 properties in Illinois Centennial Memorial Column
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.

The Annual Holiday Sale

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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.