Oakbrook Terrace Vacation Packages
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Top Oakbrook Terrace Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel
Price was CA $909, price is now CA $625 per person
CA $625
per person
Mar 28 - Apr 4
found 1 hour ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
8/10 Very Good! (478 reviews)
Was an wonderful experience. The staff was very kind and helpful. The view was amazing. Highly recommend any time of the year!
Reviewed on Jan 12, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,469, price is now CA $930 per person
CA $930
per person
Mar 21 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!
Reviewed on Feb 2, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,282, price is now CA $1,494 per person
CA $1,494
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,424, price is now CA $972 per person
CA $972
per person
Mar 21 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,377, price is now CA $944 per person
CA $944
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The breakfasts, how clean it was, and its convenience. I would recommend 10/10
Reviewed on Feb 8, 2026
Oakbrook Terrace Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Feb 9 to Feb 10
CA $122
CA $143 total
Feb 9 - Feb 10
includes taxes & fees
8/10 Very Good! (9,863 reviews)
Good location for many activities. Room was good but less than great.
Reviewed on Feb 7, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Feb 21 to Feb 22
CA $190
CA $263 total
Feb 21 - Feb 22
includes taxes & fees
8.4/10 Very Good! (2,611 reviews)
Yes
Reviewed on Feb 7, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Feb 22 to Feb 23
CA $140
CA $165 total
Feb 22 - Feb 23
includes taxes & fees
8.4/10 Very Good! (5,637 reviews)
Yes room was spotless
Reviewed on Feb 4, 2026
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.
Discover the most popular places to visit in Oakbrook Terrace
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy 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 Oakbrook Terrace
Wendella's 90-min Chicago River Architecture Tour
CA $55
per adult
94% of travellers recommend
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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.
