Oakbrook Terrace Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Oakbrook Terrace Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $2,114, price is now CA $1,198 per person
CA $1,198
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean amenities, amazing food, and great service!
Reviewed on Feb 27, 2026
La Banque Hotel
Price was CA $1,406, price is now CA $853 per person
CA $853
per person
Apr 23 - Apr 28
found 14 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $2,238, price is now CA $1,618 per person
CA $1,618
per person
May 3 - May 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
This was a trendy aesthetic hotel. It is in a great location. Had a good time.
Reviewed on Feb 26, 2026
The Peninsula Chicago
Downtown Chicago
Price was CA $1,857, price is now CA $1,381 per person
CA $1,381
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was amazing. Staff was fantastic. Best Hotel we have ever stayed at
Reviewed on Feb 26, 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 $122 per night from Feb 28 to Mar 1
CA $122
CA $143 total
Feb 28 - Mar 1
includes taxes & fees
8/10 Very Good! (9,891 reviews)
We mainly go to Chicago for medical appointments and it is *so awesome* that you can actually open the windows here.That is the main reason we chose it. Because Dad has cancer we aired it out and then ran our own air purifier. No bad smells or anything, we're just being cautious because of his health. ...
Reviewed on Feb 27, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Mar 4 to Mar 5
CA $155
CA $220 total
Mar 4 - Mar 5
includes taxes & fees
9.4/10 Exceptional! (3,420 reviews)
Good job
Reviewed on Feb 27, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Mar 5 to Mar 6
CA $146
CA $171 total
Mar 5 - Mar 6
includes taxes & fees
8.6/10 Excellent! (5,689 reviews)
Room was clean, beds weren't that comfortable. Other, than that I would stay there again.
Reviewed on Feb 27, 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(158 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(19 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
4.5/5(459 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Oakbrook Terrace
Wendella's 90-min Chicago River Architecture Tour
CA $55
per adult
94% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
