Bolingbrook Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,067, price is now CA $747 per person
CA $747
per person
Jun 13 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
I am very happy to stay above hotel . The breakfast is excellent

Reviewed on Apr 7, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,938, price is now CA $1,283 per person
CA $1,283
per person
Jun 18 - Jun 21
found 8 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Everything was spectacular amenities,room,and customer service

Reviewed on Apr 6, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $4,255, price is now CA $2,858 per person
CA $2,858
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
The room was very clean, great location, and great staff.

Reviewed on Apr 6, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $2,251, price is now CA $1,525 per person
CA $1,525
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
I was truly disappointed with fairmont gold snack and canapés - they should incorporate more vegan and vegetarian options.snacks was overall terrible just popcorns and candies. But the best part was the room and staff …

Reviewed on Apr 6, 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,869, price is now CA $2,016 per person
CA $2,016
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.4/10 Exceptional! (1,187 reviews)
Excellent choice for solo or business travelers looking for rooms with a good amount of space and a comfortable desk for working from. Great location.

Reviewed on Apr 6, 2026

Ready to book your vacation to Bolingbrook?

 

Choose your dates

Bolingbrook Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Apr 16 to Apr 17
CA $151
CA $177 total
Apr 16 - Apr 17
includes taxes & fees
8/10 Very Good! (10,052 reviews)
Air conditioner was really noisy, they told me there is a free parking when i booked, no towel in the bathroom

Reviewed on Apr 6, 2026

Congress Plaza Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $370 per night from Apr 12 to Apr 13
CA $370
CA $434 total
Apr 12 - Apr 13
includes taxes & fees
8.4/10 Very Good! (2,252 reviews)
No idea

Reviewed on Apr 6, 2026

Hilton Chicago O'Hare Airport
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Apr 8 to Apr 9
CA $121
CA $184 total
Apr 8 - Apr 9
includes taxes & fees
8.2/10 Very Good! (2,612 reviews)
Great experience and friendly staff

Reviewed on Apr 6, 2026

Hotel Felix River North/Magnificent Mile
See all 4,387 properties in Bolingbrook
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Bolingbrook

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

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.

Naval Base Great Lakes
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Bolingbrook

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $61
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Bolingbrook

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.