Bolingbrook Vacation Packages
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Your Bolingbrook Vacation
Put together a custom vacation package to Bolingbrook and get ready to experience this interesting city on your own terms. Think about spending some time in the neighborhood of Clarendon Hills, which is great for golfing and lots more. Want to explore your new surroundings? Promenade Bolingbrook, Bolingbrook Golf Club and Seven Bridges Golf Club are just three of the most popular places to visit during a trip to Bolingbrook. A couple of clicks is all it takes to build a tailor-made Bolingbrook vacation on Expedia.
Top Bolingbrook Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,727, price is now CA $1,204 per person
CA $1,204
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (493 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,911, price is now CA $1,255 per person
CA $1,255
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Terrible attitude of the front desk clerk.
Room smelled bad, dirty carpet.
Reviewed on Jun 24, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $3,802, price is now CA $2,621 per person
CA $2,621
per person
Aug 1 - Aug 5
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
The place was serene,close proximity to Fulton market and had amazing views
Reviewed on Jun 22, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,442, price is now CA $1,689 per person
CA $1,689
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The hotel and location are beautiful but there needs to be much clearer signage as to where the entrance of the hotel is and the main lobby. Extremely confusing to travellers.
Reviewed on Jun 23, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $2,376, price is now CA $1,714 per person
CA $1,714
per person
Aug 3 - Aug 7
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
Bolingbrook Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Jun 29 to Jun 30
CA $194
CA $230 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very good! (10,178 reviews)
"Great location for see the city. Staff is very friendly and helpful. The only problem we had was the a/c unit was leaking water on the floor the staff came in the room and turned off the a/c unit and left a fan to help with the summer heat. Parking was expensive but very close to the hotel. Parking ..."
Reviewed on Jun 24, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Jun 28 to Jun 29
CA $181
CA $206 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,729 reviews)
"Nice and clean property with low rate . Close to metro station and Very easy to access to Chicago city thru train."
Reviewed on Jun 24, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $361 per night from Jul 3 to Jul 4
CA $361
CA $424 total
Jul 3 - Jul 4
includes taxes & fees
8.4/10 Very good! (2,323 reviews)
"I love how convenient this hotel is. However they should FIRE their designer. Whoever thought shag carpets work with rolling luggage has never been a guest at the hotel. The room hallways have a lower profile carpet but still difficult. Even the maintenance people joke about it; not really funny ..."
Reviewed on Jun 22, 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 Bolingbrook
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 Bolingbrook
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
CA $69
per adult
94% 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.
