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Bolingbrook

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Bolingbrook Flights as Low as $138

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Sat, Sep 5 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$138 Roundtrip, found 4 hours ago
$138
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 9, priced at $138 found 4 hours ago
Frontier Airlines
Sat, Jul 4 - Tue, Jul 7
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 15 hours ago
$140
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sat, Jul 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jul 7, priced at $140 found 15 hours ago
United
Wed, Aug 12 - Sat, Aug 22
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 2 hours ago
$153
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Aug 12 from Logan Intl. to O'Hare Intl., returning Sat, Aug 22, priced at $153 found 2 hours ago
American Airlines
Wed, Aug 12 - Sat, Aug 22
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 2 hours ago
$153
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Aug 12 from Logan Intl. to O'Hare Intl., returning Sat, Aug 22, priced at $153 found 2 hours ago
Delta
Wed, Aug 19 - Tue, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 2 hours ago
$153
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Aug 19 from Logan Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $153 found 2 hours ago
JetBlue Airways
Wed, Aug 19 - Tue, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 2 hours ago
$153
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Wed, Aug 19 from Logan Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $153 found 2 hours ago
Frontier Airlines
Tue, Aug 18 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$193 Roundtrip, found 2 hours ago
$193
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Los Angeles Intl. to O'Hare Intl., returning Wed, Sep 2, priced at $193 found 2 hours ago
Bargain Flight
Wed, Sep 9 - Sat, Sep 12
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$236 Roundtrip, found 2 days ago
$236
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Wed, Sep 9 from Southwest Florida Intl. to O'Hare Intl., returning Sat, Sep 12, priced at $236 found 2 days ago
Frontier Airlines
Wed, Oct 7 - Sat, Oct 17
LAX
Los Angeles Intl.
MDW
Midway Intl.
$262 Roundtrip, found 2 days ago
$262
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Oct 7 from Los Angeles Intl. to Midway Intl., returning Sat, Oct 17, priced at $262 found 2 days ago
American Airlines
Fri, Jul 10 - Sun, Jul 12
BOS
Logan Intl.
RFD
Greater Rockford
$279 Roundtrip, found 5 days ago
$279
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Jul 10 from Logan Intl. to Greater Rockford, returning Sun, Jul 12, priced at $279 found 5 days ago
American Airlines
Fri, Jul 24 - Fri, Jul 31
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$285 Roundtrip, found 6 hours ago
$285
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Fri, Jul 24 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, Jul 31, priced at $285 found 6 hours ago
Alaska Airlines
Mon, Nov 16 - Fri, Dec 4
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$315 Roundtrip, found 1 day ago
$315
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Mon, Nov 16 from Los Angeles Intl. to O'Hare Intl., returning Fri, Dec 4, priced at $315 found 1 day ago
Frontier Airlines
Thu, Jul 30 - Thu, Aug 20
BOS
Logan Intl.
MDW
Midway Intl.
$317 Roundtrip, found 3 hours ago
$317
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Jul 30 from Logan Intl. to Midway Intl., returning Thu, Aug 20, priced at $317 found 3 hours ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$425 Roundtrip, found 2 days ago
$425
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $425 found 2 days ago
Delta
Fri, Jul 3 - Wed, Jul 8
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$560 Roundtrip, found 6 days ago
$560
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jul 3 from Southwest Florida Intl. to Midway Intl., returning Wed, Jul 8, priced at $560 found 6 days ago
American Airlines
Thu, Jul 9 - Mon, Jul 13
RSW
Southwest Florida Intl.
RFD
Greater Rockford
$593 Roundtrip, found 14 hours ago
$593
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Thu, Jul 9 from Southwest Florida Intl. to Greater Rockford, returning Mon, Jul 13, priced at $593 found 14 hours ago

Cheap Flights to Bolingbrook

Fall in love at first flight with your vacation to Bolingbrook by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Bolingbrook on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Bolingbrook, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Bolingbrook

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Bolingbrook with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Bolingbrook?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Bolingbrook are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Bolingbrook?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Bolingbrook.

What airport is best to fly into Bolingbrook?

When you’re planning your trip to Bolingbrook, convenience is the name of the game. Luckily, Bolingbrook Dupage Airport is nearby so you can deplane and get going on checking off everything on your Bolingbrook must-do list.

How much are flights to Bolingbrook?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Bolingbrook on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $138, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Bolingbrook?

The trick to saving a stack of cash on your flight to Bolingbrook? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $138 right now, why wait?

Bolingbrook Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$138

Last Minute Hotel Deals in Bolingbrook

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
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 ...
8/10 Very Good! (10,190 reviews)
"The rooms were bigger than expected! Very nice hotel and helpful staff. We arrived early than check in time was able to check in early for a fee. They had staff everywhere whom were very helpful with directions or if need any type of transportation. This was my second time staying here. Great location ..."

Reviewed on Jul 2, 2026

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Congress Plaza Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
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 ...
8.4/10 Very Good! (2,334 reviews)
"Staff were really helpful and sweet during check in. During checkout I was told there are no shuttles to take me to my terminal in quite a short and ubrupt manner. But to be honest the price is ridiculous for the outdated hotel. Seems like they think they can charge Hilton prices for what looks like ..."

Reviewed on Jun 30, 2026

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Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
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 ...
8.8/10 Excellent! (2,769 reviews)
"We like that the airport was close to the hotel, the check-in staff is not really that helpful in the breakfast is not complementary. The lobby in the rooms are very nice, but again the hotel is a little bit complicated to navigate out of the parking lot. Many Chicago hotels charge for parking daily ..."

Reviewed on Jul 2, 2026

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Hyatt Regency O'Hare Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
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 ...
7.6/10 Good! (2,641 reviews)
"*"

Reviewed on Jul 2, 2026

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Travelodge by Wyndham Downtown Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
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 ...
8.6/10 Excellent! (2,508 reviews)
"The lobby looks great and impressive."

Reviewed on Jun 30, 2026

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Palmer House a Hilton Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
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 ...
8.8/10 Excellent! (2,423 reviews)
"Hotel is conveniently located to several great places. Easy to get to and from. Rooms a little worn. Need some upkeep. Staff always seemed to be bothered if I had a question. Overall stay was really good, but friendliness of some of the guest reception staff was not that good. Kitchen and bar staff ..."

Reviewed on Jul 1, 2026

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Holiday Inn Chicago Dwtn - The Mart by IHG
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
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 ...
9/10 Wonderful! (2,315 reviews)
"Place was okay, definitely wouldn’t book here again. The rooms have a certain hospital odor & the furniture/rooms are really outdated. Definitely gives me early 2000s vibes. We booked last minute since we didn’t want to drink & drive back home. But for any tourist looking for a good place to stay. ..."

Reviewed on Jul 2, 2026

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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
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 ...
8.2/10 Very Good! (2,792 reviews)
"I would definitely stay here again! Convenient location, walkable from most things. Staff were amazing and so helpful. Basic rooms, decent size. Very clean, great bar."

Reviewed on Jul 1, 2026

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Hotel Felix River North/Magnificent Mile
See all 4,135 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.