Oakbrook Terrace Vacation Packages
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Top Oakbrook Terrace Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $1,268, price is now CA $823 per person
CA $823
per person
Jul 27 - Jul 30
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (2,509 reviews)
Staff were very accommodating.
Suite was spacious.
Reviewed on May 1, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,439, price is now CA $910 per person
CA $910
per person
Jul 27 - Jul 30
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee ” with associated taxes.
Reviewed on Apr 24, 2026
The Royal Sonesta Chicago River North
Downtown Chicago
Price was CA $1,250, price is now CA $828 per person
CA $828
per person
Jul 27 - Jul 30
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,550 reviews)
The Royal Sonesta was a complete delight! They had staff available to help at all times, and they were always cheerful and friendly. I’ll definitely be back!
Reviewed on Apr 29, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,467, price is now CA $1,649 per person
CA $1,649
per person
Jul 13 - Jul 17
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
Absolutely fantastic will be back
Reviewed on Apr 27, 2026
Oakbrook Terrace Hotel Deals
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from May 25 to May 26
CA $118
CA $182 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,652 reviews)
Rooms were infrequently cleaned and we had to request soap and new towels (no we didn’t have our (no housekeeping) sign up). Other than that it was a nice stay.
Reviewed on May 1, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from May 25 to May 26
CA $172
CA $205 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,140 reviews)
Beautiful, clean room with an incredible downtown Chicago view. Totally worth it
Reviewed on Apr 29, 2026
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Fully refundable
The price is CA $134 per night from May 25 to May 26
CA $134
CA $159 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (3,465 reviews)
Facility was clean and the staff very friendly. Rooms are a bit on the small size but I believe that is pretty common in these types of hotels in the downtown area. Unfortunate that they don't offer 2 queen beds but that is due to the room size. Did not care for the opaque/privacy glass on the bathroom ...
Reviewed on May 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
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.
