Oakbrook Terrace Vacation Packages
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Top Oakbrook Terrace Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $1,583, price is now CA $1,072 per person
CA $1,072
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,124 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,981, price is now CA $1,277 per person
CA $1,277
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,719, price is now CA $1,181 per person
CA $1,181
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (468 reviews)
Love the amenities. Great location too
Reviewed on May 3, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,092, price is now CA $1,458 per person
CA $1,458
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,670 reviews)
Amazing hotel and staff!
Reviewed on May 5, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,705, price is now CA $1,194 per person
CA $1,194
per person
Jun 18 - Jun 21
found 17 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on May 6, 2026
Oakbrook Terrace Hotel Deals
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
The price is CA $118 per night from May 26 to May 27
CA $118
CA $182 total
May 26 - May 27
includes taxes & fees
8.2/10 Very Good! (2,683 reviews)
Friendly staff. Good location
Reviewed on May 5, 2026
River Hotel
75 East Wacker Drive Chicago IL
The price is CA $184 per night from May 26 to May 27
CA $184
CA $219 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (5,167 reviews)
This hotel is conveniently located on the Riverwalk, which makes it accessible to so much. Our room was a little on the small side and the air-conditioning did not work. The staff was friendly and it’s a great location to catch an Uber.
Reviewed on May 6, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
The price is CA $183 per night from May 27 to May 28
CA $183
CA $256 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (4,070 reviews)
Very nice and clean hotel. Wonderful break fast buffet with good selection of food.
Reviewed on May 6, 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.
Naval Base Great Lakes
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
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Oakbrook Terrace
Skydeck - Willis Tower Admission
CA $61
per adult
96% 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.
