Oakbrook Terrace Vacations from ￥69,496
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The Latest Oakbrook Terrace Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥93,013, price is now ￥69,496 per person
￥69,496
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.2/10 Very Good! (2,655 reviews)
Overall Hotel Felix was a fantastic choice for our stay. The location, quality of room, friendly staff and thoughtfulness in design and details make it a 5/5.
Reviewed on May 3, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥156,598, price is now ￥91,736 per person
￥91,736
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (3,991 reviews)
The hotel was beautiful and staff were welcoming and helpful. There is a parking garage conveniently located next to the hotel and they offer a reduced rate for guests. The hotel not only has a mini bar on the main floor but also have one on the roof top which is beautiful and a nice way to end the night. I highly recommend the hotel! My husband and I have already decided to stay again in the future.
Reviewed on May 4, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Save 100% on your flight
Price was ￥109,068, price is now ￥76,246 per person
￥76,246
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,054 reviews)
The staff were fantastic, and the beds were insanely comfortable/blankets were soft and plush. The location is advantageous- lots of shopping, food, and things to do nearby. Getting an Uber from this location was a breeze and took less than five minutes. The Valet service for Staypineapple was also good. Would definitely recommend!
Reviewed on May 1, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥105,147, price is now ￥74,538 per person
￥74,538
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥174,406, price is now ￥128,576 per person
￥128,576
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
The staff was excellent and extremely helpful and informative. The hotel has amazing amenities and location is great!
Reviewed on May 3, 2026
Find the Best Oakbrook Terrace Vacation Packages
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 ￥13,628 per night from May 25 to May 26
￥13,628
￥20,993 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,670 reviews)
loved my stay!
Reviewed on May 3, 2026
River Hotel
75 East Wacker Drive Chicago IL
The price is ￥21,220 per night from May 26 to May 27
￥21,220
￥25,230 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (5,159 reviews)
Staff was very friendly!
Reviewed on May 3, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥24,412 per night from May 10 to May 11
￥24,412
￥29,024 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (4,251 reviews)
Nice clean room and friendly staff
Reviewed on May 3, 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
￥7,012
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.
