
Oak Forest Holidays
Photo by Erik Rowley
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Top Flight + Hotel Deals in Oak Forest
Price found within the past 48 hours. Click for updated prices.

Arlo Chicago
Downtown Chicago
Price was €674, price is now €395 per person
€395
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
I wish that all the staff was more accommodating! some of them were some were not!
Reviewed on 6 Oct 2025

Pendry Chicago
Downtown Chicago
Price was €815, price is now €456 per person
€456
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend
Reviewed on 7 Oct 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,875, price is now €1,050 per person
€1,050
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.
Reviewed on 6 Oct 2025

The Emily Hotel
Downtown Chicago
Price was €1,051, price is now €608 per person
€608
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
I stayed here for one night for business travel. The room was huge. Great mini bar options. I had a nice breakfast at the restaurant.
Reviewed on 10 Oct 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €708, price is now €437 per person
€437
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Clean room, friendly staff, great location and within walking distance from all shops!
Reviewed on 7 Oct 2025
Top hotels in Oak Forest

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
7.8/10 Good! (9,366 reviews)
"Shockingly updated interior of the rooms based on the historic feel of the common areas- I was so pleasantly surprised!"
Reviewed on 10 Oct 2025

Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €206 per night from 30 Oct to 31 Oct
€206
30 Oct - 31 Oct
includes taxes & fees
8.4/10 Very Good! (1,997 reviews)
"Put in new carpet and update walls"
Reviewed on 6 Oct 2025

The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St, Chicago, IL
The price is €233 per night from 19 Oct to 20 Oct
€233
19 Oct - 20 Oct
includes taxes & fees
8.8/10 Excellent! (2,107 reviews)
"Very friendly staff. Great at deco decor."
Reviewed on 7 Oct 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.
Popular places to visit

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Oak Forest

Skydeck - Willis Tower Admission
€38
per adult
100% of travellers recommend

Chicago By Night River & Lake Cruise
€38
per adult
96% of travellers recommend

Chicago Sightseeing River and Lake Cruise
€38
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.