Oakbrook Terrace Vacation Packages
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Top Oakbrook Terrace Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,769, price is now CA $1,239 per person
CA $1,239
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (395 reviews)
Great location and well maintained property!
Reviewed on May 29, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,950, price is now CA $1,361 per person
CA $1,361
per person
Jul 29 - Aug 1
found 2 days ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
Great experience and beautiful views
Reviewed on Jun 1, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,060, price is now CA $1,471 per person
CA $1,471
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
Great room, professional staff, no complaints.
Reviewed on May 31, 2026
Le Méridien Essex Chicago
Downtown Chicago
Price was CA $1,795, price is now CA $1,285 per person
CA $1,285
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (1,006 reviews)
Staff was amazing and very helpful, gave us a lot of great recommendations for places to check out and also upgraded our room for free. The room was very nice, a little tight but that is expected in Chicago. Bathroom was perfect great shower, amazing view from room and bathroom window. Very conveniently located, quick walk from the train. Highly recommend and would stay again
Reviewed on Jun 1, 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 $192 per night from Jun 29 to Jun 30
CA $192
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,149 reviews)
"Wouldn't stay again unless it's free"
Reviewed on Jun 1, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $210 per night from Jun 28 to Jun 29
CA $210
CA $249 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,502 reviews)
"Everything was fine."
Reviewed on Jun 1, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $261 per night from Jun 30 to Jul 1
CA $261
CA $349 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,314 reviews)
"Great clean room, staff were so nice!"
Reviewed on Jun 1, 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
4.5/5(159 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
4.5/5(460 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Oakbrook Terrace
Wendella's Lake and River Architecture Tour
CA $62
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.
