Search Cheap Flights to
Bolingbrook

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Bolingbrook Flights as Low as $149

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

Delta
Wed, Aug 19 - Tue, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$149 Roundtrip, found 2 days ago
$149
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Aug 19 from Logan Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $149 found 2 days ago
United
Tue, Aug 4 - Tue, Aug 11
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 1 hour ago
$153
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Aug 4 from Logan Intl. to O'Hare Intl., returning Tue, Aug 11, priced at $153 found 1 hour ago
Delta
Wed, Aug 19 - Sun, Sep 6
BOS
Logan Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Aug 19 from Logan Intl. to O'Hare Intl., returning Sun, Sep 6, priced at $157 found 2 days ago
American Airlines
Tue, Aug 4 - Tue, Aug 11
BOS
Logan Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 1 hour ago
$163
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Aug 4 from Logan Intl. to O'Hare Intl., returning Tue, Aug 11, priced at $163 found 1 hour ago
JetBlue Airways
Tue, Aug 4 - Tue, Aug 11
BOS
Logan Intl.
ORD
O'Hare Intl.
$173 Roundtrip, found 1 hour ago
$173
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Logan Intl. to O'Hare Intl., returning Tue, Aug 11, priced at $173 found 1 hour ago
American Airlines
Tue, Jun 30 - Tue, Aug 4
BOS
Logan Intl.
RFD
Greater Rockford
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jun 30 from Logan Intl. to Greater Rockford, returning Tue, Aug 4, priced at $174 found 2 days ago
Frontier Airlines
Wed, Aug 19 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$195 Roundtrip, found 5 days ago
$195
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Aug 19 from Los Angeles Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $195 found 5 days ago
Alaska Airlines
Thu, Aug 13 - Sun, Aug 30
SAN
San Diego Intl.
ORD
O'Hare Intl.
$227 Roundtrip, found 6 days ago
$227
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Thu, Aug 13 from San Diego Intl. to O'Hare Intl., returning Sun, Aug 30, priced at $227 found 6 days ago
Frontier Airlines
Tue, Aug 18 - Wed, Sep 9
LAX
Los Angeles Intl.
MDW
Midway Intl.
$240 Roundtrip, found 1 hour ago
$240
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Los Angeles Intl. to Midway Intl., returning Wed, Sep 9, priced at $240 found 1 hour ago
Frontier Airlines
Thu, Jul 30 - Tue, Aug 18
BOS
Logan Intl.
MDW
Midway Intl.
$242 Roundtrip, found 1 hour ago
$242
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Jul 30 from Logan Intl. to Midway Intl., returning Tue, Aug 18, priced at $242 found 1 hour ago
Frontier Airlines
Wed, Jul 8 - Thu, Jul 23
SNA
John Wayne
ORD
O'Hare Intl.
$260 Roundtrip, found 1 hour ago
$260
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Jul 8 from John Wayne to O'Hare Intl., returning Thu, Jul 23, priced at $260 found 1 hour ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$332 Roundtrip, found 22 hours ago
$332
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $332 found 22 hours ago
Delta
Fri, Jul 24 - Thu, Jul 30
SAN
San Diego Intl.
MDW
Midway Intl.
$386 Roundtrip, found 5 days ago
$386
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Jul 24 from San Diego Intl. to Midway Intl., returning Thu, Jul 30, priced at $386 found 5 days ago
United
Fri, Jul 3 - Fri, Jul 10
CLD
McClellan-Palomar
ORD
O'Hare Intl.
$429 Roundtrip, found 1 hour ago
$429
Roundtrip
found 1 hour ago
Select United flight, departing Fri, Jul 3 from McClellan-Palomar to O'Hare Intl., returning Fri, Jul 10, priced at $429 found 1 hour ago
Sun Country Airlines
Fri, Jun 26 - Sun, Jun 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$889 Roundtrip, found 10 hours ago
$889
Roundtrip
found 10 hours ago
Select Sun Country Airlines flight, departing Fri, Jun 26 from Los Angeles Intl. to O'Hare Intl., returning Sun, Jun 28, priced at $889 found 10 hours ago
United
Fri, Jul 24 - Tue, Aug 4
CLD
McClellan-Palomar
MDW
Midway Intl.
$1,561 Roundtrip, found 1 hour ago
$1,561
Roundtrip
found 1 hour ago
Select United flight, departing Fri, Jul 24 from McClellan-Palomar to Midway Intl., returning Tue, Aug 4, priced at $1,561 found 1 hour 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 August, 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 16 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 $149, 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 $149 right now, why wait?

Bolingbrook Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$108

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! (10,296 reviews)
"Have to pay for parking plus the ac barely works"

Reviewed on Jun 17, 2026

Get rates
Congress Plaza Hotel
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! (2,688 reviews)
"Hotel main trash service pickup was directly below my room window and was extremely loud when unloading and loading rolloff dumpsters at 4am. No way to sleep through the noise. Shuttle service was very good to and from the airport. Toilet clogged after one use with no plunger available. Remodeling ..."

Reviewed on Jun 17, 2026

Get rates
Hyatt Regency O'Hare Chicago
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! (2,349 reviews)
"So convenient to the airport — an easy walk to terminal 2 and short train ride to the other terminals. No stress before an early morning flight. Great gym and pretty good casual restaurant. Clean and comfortable rooms."

Reviewed on Jun 16, 2026

Get rates
Hilton Chicago O'Hare Airport
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! (2,769 reviews)
"Hotel allows loud room parties. A party on the floor I was staying on started at 2:30 and went on until 4:30am on a Wednesday night. Loud voices (not even trying to be quiet) in the hallways, doors slamming going back and forth from rooms. Not even sure these were registered hotel guests as many ..."

Reviewed on Jun 17, 2026

Get rates
Hotel Felix River North/Magnificent Mile
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! (2,604 reviews)
"Room was very clean, roomy, and well maintained. Kitchen area was nicer than expected and parking was a bit expensive but very convenient."

Reviewed on Jun 18, 2026

Get rates
Travelodge by Wyndham Downtown Chicago
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! (2,257 reviews)
"Location in West Loop is fantastic, a block away from Whole Foods and a number of great restaurants in Greek town. The staff was fantastic in addressing our needs immediately including a clogged sink and sliding door that came off the tracks. The infrastructure is a bit old and outdated. The only ..."

Reviewed on Jun 16, 2026

Get rates
Crowne Plaza Chicago West Loop by IHG
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! (2,405 reviews)
"The hotel was perfect for what we needed! The king-size room was very comfortable. The staff consistently text and was responsive to anything we needed. Great service! The 15th floor lobby and restaurant are great for hanging out and catching a drink at the bar or grabbing a bite or a snack. Even ..."

Reviewed on Jun 16, 2026

Get rates
Holiday Inn Chicago Dwtn - The Mart by IHG
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
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 ...
8.6/10 Excellent! (2,866 reviews)
"Gave us an upgrade at checkin that meant a lot :) Also halpily gave me ibuprofen at 3:00 a.m! Lovely property in a nice location by the lake!"

Reviewed on Jun 18, 2026

Get rates
Hilton Chicago
See all 4,288 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.