Bolingbrook Vacations
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Bolingbrook Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $1,059, price is now $817 per person
$817
per person
Dec 21 - Dec 28
found 19 hours ago
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
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 staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The room was not ready upon arrival so we had to wait 45 min after check in to get into our room. Additionally, we left the room at 930a , returned at 6p and the room had not been cleaned. There were fresh towels laid on top of the bed but nothing else had been touched. Seemed a little disorganized bc when we asked why the room had been left untouched they said “they were just really busy bc they were booked” but idk, if I’m paying to stay there, it’s not my job to make sure you can handle the level of occupancy you booked. It’s pretty centrally located but I wouldn’t stay here again
Reviewed on Nov 15, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,606, price is now $1,102 per person
$1,102
per person
Dec 21 - Dec 28
found 19 hours ago
Roundtrip flight included
San Diego (SAN) 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.
Top notch hotel. Never stayed at a Riu property before, but will definitely look into one whenever I am out of town. Clean, modern, and spacious rooms, terrific customer service and the breakfast buffet was very good too.
Reviewed on Nov 15, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,576, price is now $1,136 per person
$1,136
per person
Dec 21 - Dec 28
found 19 hours ago
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
The Blackstone, Autograph Collection
Downtown Chicago
Price was $1,126, price is now $829 per person
$829
per person
Dec 24 - Dec 31
found 14 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Swissotel - Chicago
Downtown Chicago
Price was $1,323, price is now $1,012 per person
$1,012
per person
Dec 21 - Dec 28
found 19 hours ago
Roundtrip flight included
San Diego (SAN) 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.
Beautiful building Nice room sweet customer services. The no microwave and charging customers to warm their food is honestly insane and inconsiderate. It was a 5/10 probably will not be a returning customer.
Reviewed on Nov 15, 2026
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
Price was $1,080, price is now $829 per person
$829
per person
Dec 21 - Dec 28
found 19 hours ago
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
A
Reviewed on Nov 12, 2026
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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 4279 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
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 ...
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 ...
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
172 W Adams St Chicago IL
41.32 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the ...
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 ...
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 ...
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 ...
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 ...
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
15.89 km from city center
Book a stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms ...
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 ...
The Chicago Hotel Collection River North
312 W. Chestnut St. Chicago IL
42.15 km from city center
Stay at this hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Hyatt Place Chicago/Downtown - The Loop
28 North Franklin Street Chicago IL
41.32 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 breakfast ...
Sentral Michigan Avenue
808 SOUTH MICHIGAN AVENUE Chicago IL
41.53 km from city center
Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests ...
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 ...
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.
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Tue, Feb 23 - Wed, Feb 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$257 Roundtrip, found 15 hours ago
$257
Roundtrip
found 15 hours ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Tue, Jan 26 - Tue, Feb 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$262 Roundtrip, found 4 days ago
$262
Roundtrip
found 4 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$274 Roundtrip, found 2 days ago
$274
Roundtrip
found 2 days ago