Oakbrook Terrace Vacation Packages
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Top Oakbrook Terrace Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,870, price is now CA $1,271 per person
CA $1,271
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,505 reviews)
The breakfast menu & service at the Lyrica was excellent. The parking was very convenient, although a little pricey at $65 for overnight. The rooms and view were simply awesome. The service at the front desk was excellent. I look forward to my next stay.
Reviewed on May 20, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,763, price is now CA $1,251 per person
CA $1,251
per person
Jul 23 - Jul 26
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,126 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,513, price is now CA $1,789 per person
CA $1,789
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,864 reviews)
Great experience! Would stay here agin
Reviewed on May 18, 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 $184 per night from May 25 to May 26
CA $184
CA $218 total
May 25 - May 26
includes taxes & fees
8/10 Very Good! (10,170 reviews)
"This is one of those grand old hotels that used to be amazing, but has now fallen on very hard times. There's a reason it is one of the cheapest (though still expensive) hotels in the Chicago Loop. The staff seemed absent or disinterested, the facility has peeling paint everywhere, and the vibe is ..."
Reviewed on May 20, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from May 25 to May 26
CA $205
CA $283 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,195 reviews)
"Extraordinary staff so helpful to my disabled husband. We went to celebrate his birthday in Chicago. I wouldn’t go anywhere else."
Reviewed on May 20, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 25 to May 26
CA $167
CA $198 total
May 25 - May 26
includes taxes & fees
7.8/10 Good! (1,442 reviews)
"The laundry was not working"
Reviewed on May 20, 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
Skydeck - Willis Tower Admission
CA $60
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.
