Oak Park Holidays

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Oak Park Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was S$2,188, price is now S$1,835 per person
S$1,835
per person
4 May - 9 May
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.2/10 Very Good! (2,575 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back.

Reviewed on 4 Mar, 2026

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
Price was S$2,926, price is now S$2,396 per person
S$2,396
per person
2 May - 8 May
found 4 hours ago
Return flight included
Singapore (SIN) to Chicago (ORD)
8.6/10 Excellent! (4,378 reviews)
Washroom door was not getting locked, apart from that everything was good.

Reviewed on 16 Mar, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was S$3,103, price is now S$2,187 per person
S$2,187
per person
4 May - 9 May
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The shower pressure is awful and doesn’t get hot

Reviewed on 16 Mar, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was S$3,823, price is now S$3,038 per person
S$3,038
per person
4 May - 9 May
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,844 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.

Reviewed on 16 Mar, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was S$2,445, price is now S$2,061 per person
S$2,061
per person
4 May - 9 May
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The hotel is centrally located in Downtown Chicago with several eateries close by and walking distance from major attractions. We will definitely stay here again.

Reviewed on 16 Mar, 2026

Top hotels in Oak Park

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$242 per night from 27 Mar to 28 Mar
S$242
27 Mar - 28 Mar
includes taxes & fees
8/10 Very Good! (9,951 reviews)
The condition of the halls of the hotel and building in general showed its age, but the room had been updated and was clean. The sink and tub drainage was poor. The room was heated very well especially on a cold day. The front desk lady that checked me in seemed in a foul mood but I am sure with ...

Reviewed on 17 Mar, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$229 per night from 6 Apr to 7 Apr
S$229
6 Apr - 7 Apr
includes taxes & fees
9.4/10 Exceptional! (3,545 reviews)
The shower pressure is awful and doesn’t get hot

Reviewed on 16 Mar, 2026

Hotel Riu Plaza Chicago
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
The price is S$196 per night from 23 Mar to 24 Mar
S$196
23 Mar - 24 Mar
includes taxes & fees
8.6/10 Excellent! (5,753 reviews)
Good

Reviewed on 16 Mar, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 5,085 properties in Oak Park
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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place showing a high rise building and a city

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Oak Park

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$33
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

S$56
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

S$51
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Oak Park

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