Bolingbrook Holidays

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Top Flight + Hotel Deals in Bolingbrook

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
15 Sept - 19 Sept
found 2 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,950 reviews)
Very friendly staff!

Reviewed on 3 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
15 Sept - 19 Sept
found 2 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Great, comfortable beds, spacious rooms. The bathroom was very clean and spaciousZ loved it

Reviewed on 3 Aug 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
15 Sept - 19 Sept
found 2 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,342 reviews)
Property is loud. I wouldn't say five star. Rooms are narrow and relatively cramped.

Reviewed on 2 Aug 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
15 Sept - 19 Sept
found 2 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,253 reviews)
I loved how smooth the check in process was and all the amenities. Great rooms.

Reviewed on 1 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
15 Sept - 19 Sept
found 2 hours ago
Return flight included
Dublin (DUB) 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 27 Jul 2025

Top hotels in Bolingbrook

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 €180 per night from 4 Aug to 5 Aug
€180
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,933 reviews)
"👍"

Reviewed on 1 Aug 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
The price is €148 per night from 24 Aug to 25 Aug
€148
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,326 reviews)
"Nice location"

Reviewed on 1 Aug 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
8/10 Very Good! (1,977 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 1 Aug 2025

Get rates
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.

Popular places to visit

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 showing street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home 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

€36
per adult
96% of travellers recommend
Architecture River Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€39
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

€26
per adult
92% of travellers recommend
Skyline Lake Tour
See all activities in Bolingbrook

Frequently asked questions

How much does a Bolingbrook holiday package cost?
You can grab a holiday package to this popular destination from €777 on Expedia. However, how much your holiday 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 holiday packages and you could get some great off-season deals.
How many days is enough for Bolingbrook?
The ideal length of your Bolingbrook holiday 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 holiday package to Bolingbrook?
Bolingbrook is a good holiday 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 holiday 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 holiday package well in advance.
Is it cheaper to book a Bolingbrook holiday as a package?
An Expedia holiday 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 holiday package to Bolingbrook?
If you've got your Bolingbrook holiday 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, favourite 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 personalised Bolingbrook holiday package.

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