Oakbrook Terrace Vacation Packages
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Top Oakbrook Terrace Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,662, price is now CA $1,076 per person
CA $1,076
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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
Swissotel - Chicago
Downtown Chicago
Price was CA $2,632, price is now CA $1,645 per person
CA $1,645
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
The view is fantastic. You can see the Chicago river on one side, abd skyscraper on tge other side. The small items that the hotel provides, makes the stay, pleasant and homely.
Reviewed on May 10, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,355, price is now CA $1,579 per person
CA $1,579
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on May 8, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,700, price is now CA $1,206 per person
CA $1,206
per person
Jun 25 - Jun 28
found 2 days 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
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,384, price is now CA $1,717 per person
CA $1,717
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Horrible, horrible housekeeping staff many times I had to have head of housekeeping come and monitor
Very disappointing
Reviewed on May 10, 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 $183 per night from May 12 to May 13
CA $183
CA $217 total
May 12 - May 13
includes taxes & fees
8/10 Very Good! (10,209 reviews)
Parking lot nearby - no coffe bar - in room coffee machine didn’t work. Good location for walking to Grant Park
Reviewed on May 11, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from May 25 to May 26
CA $193
CA $269 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,106 reviews)
Was a really nice hotel. My only concerns was the phones in the room didn’t work. No way to call front desk, front people weren’t super helpful and there was no microwave. Rooftop bar and room were excellent
Reviewed on May 10, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from May 25 to May 26
CA $178
CA $212 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (4,294 reviews)
Amazing 😍😍😍😍. I would definitely recommend
Reviewed on May 11, 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 $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.
