Oakbrook Terrace Vacation Packages
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Top Oakbrook Terrace Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,202, price is now CA $833 per person
CA $833
per person
Aug 25 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
the only issue i had it was that they didn’t do room service in the room, no new towels , no toilet paper and stuff like that
Reviewed on Jun 12, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,919, price is now CA $1,261 per person
CA $1,261
per person
Sep 3 - Sep 7
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (491 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.
Reviewed on Jun 14, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,014, price is now CA $1,402 per person
CA $1,402
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (484 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,820, price is now CA $1,294 per person
CA $1,294
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
The location was very convenient
Reviewed on Jun 14, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $4,048, price is now CA $2,901 per person
CA $2,901
per person
Sep 1 - Sep 8
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,888 reviews)
The fitness center & spa was top notch. The on site restaurant had amazing food and service.
Reviewed on Jun 12, 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 $190 per night from Jun 29 to Jun 30
CA $190
CA $226 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,264 reviews)
"Great stay!"
Reviewed on Jun 14, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $202 per night from Jun 30 to Jul 1
CA $202
CA $240 total
Jun 30 - Jul 1
includes taxes & fees
7.8/10 Good! (1,578 reviews)
"Had a great time over two days in Chicago. The only downside was that my room was not cleaned when I returned."
Reviewed on Jun 14, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Jul 2 to Jul 3
CA $201
CA $229 total
Jul 2 - Jul 3
includes taxes & fees
8.8/10 Excellent! (2,666 reviews)
"Overall stay was great with my brother. I will come back agin. Staff were helpful especially with our shuttle ride to the airport."
Reviewed on Jun 13, 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.
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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.
