Oakbrook Terrace Vacation Packages
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Top Oakbrook Terrace Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,936, price is now CA $1,280 per person
CA $1,280
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (474 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.
Reviewed on May 18, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,965, price is now CA $1,891 per person
CA $1,891
per person
Jul 28 - Aug 2
found 14 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,505 reviews)
I loved it here and will definitely stay again.
Reviewed on May 18, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $3,410, price is now CA $2,288 per person
CA $2,288
per person
Jul 28 - Aug 2
found 14 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,721 reviews)
Great location with a great view. Walking distance to all attractions and restaurants. The room was spacious and comfy beds
Reviewed on May 18, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $2,379, price is now CA $1,605 per person
CA $1,605
per person
Jul 28 - Aug 2
found 14 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very Good! (2,707 reviews)
Staff is excellent. Breakfast was below standards - muffins, fruit, juice, and a couple breakfast sandwiches the staff put in the microwave. I’d pass on the breakfast. Nice location. Rooms were okay - the bed in our room was full of cat scratches.
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 $183 per night from May 26 to May 27
CA $183
CA $218 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,162 reviews)
"A old, classic hotel and a low room rate, I was not expecting 'up to date modern'. Plusses: Room was large and clean, no noise from other guests, bag storage free, price compared to other hotels very low. Minuses: Unable to turn heater on _only a thin quilt blanket for bed, noise from toilet filling ..."
Reviewed on May 19, 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! (4,186 reviews)
"My husband and I really enjoyed staying at Hotel Riu Plaza Chicago. Staff was friendly and helpful. Hotel is very clean. Breakfast & bar is so delicious we definitely will come back. Chi Love you! Thank you so much."
Reviewed on May 19, 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! (1,433 reviews)
"BEWARE: I booked and paid for this hotel a month in advance. My train was delayed a few hours, so I arrived at the hotel about 7pm. However, I completed an echeck-in at the hotels request at 1pm. Upon arriving, there was a short line of people waiting to check-in and they were upset and asking to ..."
Reviewed on May 19, 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 $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.
