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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,418 reviews)
Hotel felt hot. initially air conditoner wasn't working but was fixed. Still didn't feel like it got very cold in the room. Bathtub was very slippery.

Reviewed on Aug. 7, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Loved the attention to details that made the experience exceptional.

Reviewed on Aug. 6, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Everything is nice specially stuff hosptality

Reviewed on Aug. 8, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Transport access walking distance to take train to midway airport was easy and convenient

Reviewed on Aug. 7, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Oct 11 - Oct 14
found 20 hours ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
Loved the rooftop bar and restaurant. The service at the Lyric Restaurant on the Pier was fantastic. The Saturday night Fireworks and Drone show was great. This is a great place to walk straight up into the city center, Michigan Ave. Also a great place to walk the Lake front.

Reviewed on Aug. 8, 2025

Ready to book your vacation to Bolingbrook?

 

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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 $185 per night from Sep 1 to Sep 2
CA $185
CA $217 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,926 reviews)
"Took water awhile to get hot for shower, and parking is ridiculously expensive. Other than that enjoyed staying at hotel"

Reviewed on Aug. 8, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Aug 22 to Aug 23
CA $239
CA $314 total
Aug 22 - Aug 23
includes taxes & fees
8.2/10 Very Good! (1,833 reviews)
"Great time. Wonderful people!"

Reviewed on Aug. 7, 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is CA $195 per night from Aug 24 to Aug 25
CA $195
CA $229 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,356 reviews)
"Nice hotel and with easy access"

Reviewed on Aug. 6, 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,182 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
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Discover the most popular places to visit in Bolingbrook

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
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

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Bolingbrook

Frequently asked questions

How much does a Bolingbrook vacation package cost?
You can snap up a vacation package to this destination from CA $839 on Expedia. However, how much your vacation to Bolingbrook costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Bolingbrook?
If you're looking to snag a cheap Bolingbrook vacation package, consider travelling in December, January and February. You'll usually find better rates on hotels and flights during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Bolingbrook?
The ideal length for your Bolingbrook vacation depends on what you'd like to see. Usually, a handful of days to a week will give you enough time to tick off all the major sights and discover some hidden spots along the way.
Is it worth booking a vacation package to Bolingbrook?
Bolingbrook is a good vacation destination with attractions like Promenade Bolingbrook among the many things to keep you busy. Whether you're travelling with the family or planning a trip with friends, a Bolingbrook vacation promises a good time for everyone.
How to find the best Bolingbrook package deals?
Start your search for a Bolingbrook package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Bolingbrook package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Bolingbrook escape off to a flying start.
Is it cheaper to book a Bolingbrook vacation as a package?
You can enjoy significant savings on your Bolingbrook retreat by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Bolingbrook?
Score incredible discounts by booking your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Bolingbrook trip.
How to plan a trip to Bolingbrook?

  1. Pick your travel dates: What you want to do in Bolingbrook and your preferred season can help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and activities. Your hotel will probably be the largest expense during your trip to Bolingbrook.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you want to experience in Bolingbrook. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a Bolingbrook vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.