Bolingbrook Vacations from ￥278,193

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The Latest Bolingbrook Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Sep 9 - Sep 16
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on Jul 27, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 9 - Sep 16
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Great stay :) Mr 47 didn’t disappoint

Reviewed on Aug 1, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 9 - Sep 16
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul 26, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
Sep 9 - Sep 16
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (3,342 reviews)
Bed was amazing. Room view was not good, and for the ridiculous price we paid you would expect to be looking at something other than the back of buildings.

Reviewed on Aug 2, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 9 - Sep 16
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
I loved how smooth the check in process was and all the amenities. Great rooms.

Reviewed on Aug 1, 2025

Find the Best Bolingbrook Vacation Packages

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 ￥19,788 per night from Sep 1 to Sep 2
￥19,788
￥23,228 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,938 reviews)
"Very convenient location. Easy check-in, even with a very crowded lobby. Polite staff."

Reviewed on Aug 1, 2025

Congress Plaza 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 ￥21,520 per night from Aug 24 to Aug 25
￥21,520
￥25,262 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,328 reviews)
"Nice location"

Reviewed on Aug 1, 2025

Crowne Plaza Chicago West Loop by IHG
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 ￥15,993 per night from Aug 17 to Aug 18
￥15,993
￥23,275 total
Aug 17 - Aug 18
includes taxes & fees
8/10 Very Good! (1,976 reviews)
"It never felt like I was at some cookie cutter hotel. Comfortable bed, perfect location for my needs, loved the complimentary coffee in the morning. Will definitely come back the next time I am in town"

Reviewed on Aug 1, 2025

Hotel Felix River North/Magnificent Mile
See all 4,200 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.

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

￥7,149
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

￥6,597
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

￥6,646
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Bolingbrook

Frequently asked questions

How much does a Bolingbrook vacation package cost?
You can grab a vacation package to this popular destination from ￥278,193 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?
You can typically find reduced prices and better availability in December, January and February. Take a look at our cheap Bolingbrook vacation packages and you could get some great off-season deals.
How many days is enough for Bolingbrook?
The ideal length of your Bolingbrook vacation depends on what you'd like to do. Usually, a few days to a week will give you time to hit all the leading attractions and discover some hidden gems 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 getting away 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.
How to plan a trip to Bolingbrook?

  1. Pick the perfect time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to go to Bolingbrook.
  2. Budget wisely: In addition to the price of your stay, you'll need to consider other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Bolingbrook.
  3. Decide your trip length: Think about how long you'd like to spend discovering Bolingbrook. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalized Bolingbrook vacation package.

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