Bolingbrook Vacations from $156

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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.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $261, price is now $156 per person
$156
per person
Oct 30 - Nov 2
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.2/10 Very Good! (384 reviews)
I like the place, it is very quiet and safe, but the room requires better cleaning, the balcony was not clean and blinds need to be washed, anyhow i liked it.

Reviewed on Aug 21, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,322, price is now $641 per person
$641
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on Aug 22, 2025

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,030, price is now $621 per person
$621
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (3,059 reviews)
Loved the property, big size room and very cool decoration! Great location

Reviewed on Aug 22, 2025

The Stella Hotel & Ballroom

The Stella Hotel & Ballroom

3.5 out of 5
Downtown Kenosha
Save 100% on your flight
Price was $316, price is now $191 per person
$191
per person
Oct 30 - Nov 2
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (CHI)
9.4/10 Exceptional! (1,005 reviews)
Nice hotel, wish it had it's own parking lot.

Reviewed on Aug 23, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $551, price is now $334 per person
$334
per person
Oct 2 - Oct 5
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (433 reviews)
This is my go to place in the south suburbs.

Reviewed on Jul 30, 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

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

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

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

$41
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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
$143 nightly
The price is $168 total per night from Aug 25 to Aug 26
$168 total
Aug 25 - Aug 26
Total with taxes and fees
7.8/10 Good! (8,996 reviews)
Great view! Safe location for food music and park
"Got a very good rate during an event that had filled up many nearby hotels. Lovely sparkling-clean room, rather small, a firm king bed, dresser, & table. It felt cozy, not crowded, enough drawers and closet space, nice-size bathroom with shower-tub. Room has nice ornate details. 10th-floor sunrise ..."

Reviewed on Aug 24, 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
$198 nightly
The price is $229 total per night from Sep 2 to Sep 3
$229 total
Sep 2 - Sep 3
Total with taxes and fees
8.4/10 Very Good! (1,881 reviews)
"Beautiful unique hotel, friendly staff and quiet for people who need to rest!"

Reviewed on Aug 21, 2025

Palmer House a Hilton Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $194 total per night from Sep 2 to Sep 3
$194 total
Sep 2 - Sep 3
Total with taxes and fees
8.4/10 Very Good! (2,105 reviews)
"Nice"

Reviewed on Aug 22, 2025

Hilton Chicago
See all 4,229 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.

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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 $156 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.