Bolingbrook Vacations from $280

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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.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
Price was $461, price is now $280 per person
$280
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,306 reviews)
An excellent value! Clean and comfortable. Easy airport transport.

Reviewed on Aug 30, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,335, price is now $673 per person
$673
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,192 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

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,000, price is now $519 per person
$519
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on Aug 27, 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,021, price is now $584 per person
$584
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,890 reviews)
I really like this hotel overall, but 2 of the last 3 times I was here my room wasn’t ready until hours (up to 5) after check-in. I’ve also had issues with things like the bathtub not draining. Not deal breakers, but kind of annoying.

Reviewed on Aug 30, 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $836, price is now $506 per person
$506
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,113 reviews)
Incredibly helpful and personable staff. Comfortable, clean, well kept room.

Reviewed on Aug 31, 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

$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
$170 nightly
The price is $200 total per night from Sep 2 to Sep 3
$200 total
Sep 2 - Sep 3
Total with taxes and fees
Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$209 nightly
The price is $245 total per night from Sep 11 to Sep 12
$245 total
Sep 11 - Sep 12
Total with taxes and fees
Hilton Chicago
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
$135 nightly
The price is $158 total per night from Sep 1 to Sep 2
$158 total
Sep 1 - Sep 2
Total with taxes and fees
8/10 Very Good! (1,943 reviews)
"My niece and I loved it here! Staff was excellent. Very knowledgeable, efficient, friendly. Beds & pillows were comfortable. Enjoyed the scent of the bathroom toiletries. Nice view of city from our room. Convenient location with lots of good restaurants close by. Not far to get to train. Love that ..."

Reviewed on Aug 30, 2025

Hotel Felix River North/Magnificent Mile
See all 4,301 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 $280 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.