Boulder Hill Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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 Boulder Hill Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,161, price is now CA $787 per person
CA $787
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (116 reviews)
We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from.
Reviewed on May 17, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,919, price is now CA $1,699 per person
CA $1,699
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,741, price is now CA $1,702 per person
CA $1,702
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (478 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
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,199, price is now CA $1,592 per person
CA $1,592
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
Location, cleanliness, overall staff assistance and service and of course breakfast
Reviewed on May 26, 2026
Boulder Hill Hotel Deals
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from May 27 to May 28
CA $117
CA $130 total
May 27 - May 28
includes taxes & fees
9/10 Wonderful! (2,756 reviews)
"Great staff and spotless rooms."
Reviewed on May 26, 2026
The Westin Chicago Lombard
70 Yorktown Center Lombard IL
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Jun 14 to Jun 15
CA $218
CA $242 total
Jun 14 - Jun 15
includes taxes & fees
9/10 Wonderful! (1,267 reviews)
"Requested a room with a walk in shower as I have a broken foot and am wearing a walking boot. Was told none were available but online through the hotels own website it showed they were and were bookable for my entire stay. Rude front desk staff. Probably will never stay there again. This hotel has ..."
Reviewed on May 25, 2026
Hyatt Regency Lisle near Naperville
1400 Corporetum Drive Lisle IL
The price is CA $135 per night from May 31 to Jun 1
CA $135
CA $150 total
May 31 - Jun 1
includes taxes & fees
7.8/10 Good! (1,212 reviews)
"Very old hotel that needs renovation ASAP. The staff was helpful, and the breakfast was good. However, there was a strong smoking smell in both the room and the bathroom."
Reviewed on May 26, 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.
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.
