Bolingbrook Vacations from $542

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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.

The Latest Bolingbrook vacation packages

Price found within the past 48 hours. Click for updated prices.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,290, price is now $542 per person
$542
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,046 reviews)
One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,485, price is now $686 per person
$686
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Absolutely lovely and helpfully staff

Reviewed on Oct 8, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,206, price is now $658 per person
$658
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Perfect location and atmosphere

Reviewed on Oct 7, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,367, price is now $1,317 per person
$1,317
per person
Dec 13 - Dec 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on Oct 6, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,402, price is now $1,381 per person
$1,381
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Awesome room amazing tub even better service

Reviewed on Oct 2, 2025

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Discover the most popular places to visit in Bolingbrook

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

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

Michigan Avenue

4.5/5(332 reviews)

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 featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Bolingbrook

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
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,331 reviews)
"Very clean"

Reviewed on Oct 7, 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
$200 nightly
The price is $231 total per night from Oct 30 to Oct 31
$231 total
Oct 30 - Oct 31
Total with taxes and fees
8.4/10 Very Good! (2,001 reviews)
"Put in new carpet and update walls"

Reviewed on Oct 6, 2025

Palmer House a Hilton Hotel
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
Fully refundableReserve now, pay when you stay
$176 nightly
The price is $207 total per night from Nov 9 to Nov 10
$207 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (2,113 reviews)
"Staff was very pleasant."

Reviewed on Oct 8, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
See all 4,257 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.

Bolingbrook Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
74,300
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Rialto Square Theater, Joliet Area Historical Museum and DuPage Childrens Museum

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Frequently asked questions

How much does a Bolingbrook vacation package cost?
You can grab a vacation package to this popular destination from $542 on Expedia. However, how much your vacation to Bolingbrook costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Bolingbrook?
January, September and December are the best times to search for cheap Bolingbrook vacation packages. Traveling in quieter months means you can usually find reduced prices on hotels and flights.
How many days is enough for Bolingbrook?
The ideal duration of your Bolingbrook vacation depends on what you'd like to do. Typically, a handful of days to a week will give you enough time to check out all the leading sights and explore 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 entertained. Whether you're heading away with the family or planning a trip with friends, a Bolingbrook vacation promises fun for everyone.
How to find the best Bolingbrook package deals?
Use Expedia's handy filters to help you find some tempting Bolingbrook package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Bolingbrook package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Bolingbrook vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking stays and flights individually. Better still, you can tailor your Bolingbrook escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Bolingbrook?
If you've got your Bolingbrook vacation dates locked in, book as early as you can to snap up some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later Bolingbrook vacation packages?
Your Bolingbrook getaway should be an escape from your daily routine, not a source of money worries. So to allow you that extra flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

Explore a world of travel with Expedia

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.