Bolingbrook Vacations

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Bolingbrook Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

Downtown Chicago
Save 100% on your flight
$464
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$804
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
We were blown away that every single person associated with the hotel was kind, helpful, great at their job, accommodating, and basically wonderful. The hotel was amazingly clean, environmentally forward-thinking, safe, and handy to EVERYTHING in downtown Chicago. The best surprise was the massive breakfast buffet that was included in the price of the room. The breakfast accommodated a steady stream of guests and never ran out of the ample variety of food. It was the perfect way to begin each day. Another treat: the rooftop bar and the hotel bar. Excellent service and skilled bar-tenders. It's a gem and don't hesitate to book a room in this hotel.

Reviewed on Aug 19, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$874
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
$997
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on Aug 17, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
$609
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in. 4 days later, the on-line booking co. Said the manager did not agree to release my reservation. Unethical procedurers.

Reviewed on Aug 12, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
$843
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
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Bolingbrook Vacation Packages

Trying to save both time and money on your upcoming holiday to Bolingbrook? The AARP Travel Center Powered by Expedia® can help you do both. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Bolingbrook incredible. Our Travel Center is a one-stop shop where you can put together the best Bolingbrook vacation package for you. We have an amazing list of flights and hotels, as well as Bolingbrook things to do to pick from.

Bolingbrook Hotel Deals

With 4256 hotels and resorts in Bolingbrook to choose from, you will find one that is perfect for you.

We have fantastic rates on everything from all-inclusive resorts that check off all the vacation must-haves to affordable accommodations which are great for those on a budget. You can look through our vast catalog of options and choose the lodging that is perfect for you and your family. With AARP Travel Center's Bolingbrook hotel packages, you not only get a great rate on your flight, but also a terrific place to stay.

Things to do in Bolingbrook

Bolingbrook is bigger than it seems with around 74,306 people making this city their home. With the city's burgeoning art scene and a rich past that is a beacon for history aficionados you may have a hard time fitting everything into one trip.

Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.

Package Your Bolingbrook Vacation and Save

With so much to see and do in Bolingbrook, you'll be wanting to plan your outings, not spending time to searching for the hotel with the lowest rate. AARP Travel Center allows you to quickly get all you want, and save money while doing it. You can coordinate your entire vacation, including activities in Bolingbrook from just one place. So what are you waiting for? Bundle now and save!

Top Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
41.73 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

171 W Randolph St Chicago IL
41.56 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Hilton Chicago

Hilton Chicago

720 S Michigan Ave Chicago IL
41.55 km from city center
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
33.87 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL
35.85 km from city center
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street Chicago IL
40.38 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

506 West Harrison Street Chicago IL
40.55 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr Chicago IL
41.03 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street Chicago IL
41.44 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL
41.61 km from city center
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

111 W Huron St Chicago IL
42.26 km from city center
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL
41.82 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

127 West Huron, at LaSalle Chicago IL
42.23 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, and a 24-hour fitness center. Our guests praise the helpful staff and ...
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

350 West Wolf Point Plaza, Building 2 Chicago IL
41.42 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

5440 N River Rd Rosemont IL
35.32 km from city center
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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