Oak Forest Vacation Packages

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Your Oak Forest Vacation

Let our vacation packages to Oak Forest inspire your next getaway. There's loads to love about this lively city, starting with the neighborhood of South Deering, which is great for golfing and nature. If your trip to Oak Forest includes some sightseeing, don't miss well-known attractions like Hollywood Casino Amphitheatre, Odyssey Fun World and Coyote Run Golf Course. Check out Expedia's wide range of travel options and book your ideal vacation to Oak Forest today.

Top Oak Forest Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,512, price is now CA $1,071 per person
CA $1,071
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again.

Reviewed on May 14, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,750, price is now CA $1,175 per person
CA $1,175
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
It was very pleasant and safe. I liked that you needed a room key to use the elevator which made us feel safe. The hotel is located very central and walking distance to everything. The staff was very friendly.

Reviewed on May 16, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,881, price is now CA $1,291 per person
CA $1,291
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
Great view and room was very clean!

Reviewed on May 17, 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,517, price is now CA $1,776 per person
CA $1,776
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,225 reviews)
Nice hotel in a great location.

Reviewed on May 15, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,020, price is now CA $1,472 per person
CA $1,472
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Great hospitality!!! Will be back! Thank you

Reviewed on May 17, 2026

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Oak Forest Hotel Deals

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 CA $184 per night from May 26 to May 27
CA $184
CA $218 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,138 reviews)
The bar was very welcoming and the historic ambience and location was exceptional

Reviewed on May 16, 2026

Congress Plaza Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from May 25 to May 26
CA $198
CA $235 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (3,505 reviews)
This is about the 5th time i have stayed here. Each time the cost has increased. The bread pudding in the restaurant is to die for. Grab yourself a slice.

Reviewed on May 16, 2026

Club Quarters Hotel, Central Loop, Chicago
Central Loop Hotel

Central Loop Hotel

4 out of 5
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from May 21 to May 22
CA $186
CA $221 total
May 21 - May 22
includes taxes & fees
8.6/10 Excellent! (2,140 reviews)
I had a very pleasant stay at this hotel. The staff was exceptionally helpful, friendly, and always ready to assist. The breakfast was also unusual in a very positive way — varied, memorable, and a nice change from the standard hotel offering. Overall, I’m very happy with my stay and would gladly ...

Reviewed on May 16, 2026

Central Loop Hotel
See all 2,345 properties in Oak Forest
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.
All Inclusive Vacations
All Inclusive Vacations
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Beach Vacations
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Family Vacations

Discover the most popular places to visit in Oak Forest

Wrigley Field

Wrigley Field

4.5/5(159 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(3 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(460 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Oak Forest

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
98% of travellers recommend
Flyover in Chicago
See all activities in Oak Forest

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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.