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Cheap flights from Illinois to Boston from $69

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Boston departing on 9/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Illinois to Boston

Cheap round-trip flights

Logo
11:57 am - 11:57 pmORD-BOS
11h 00m1 stop
Logo
8:38 am - 4:45 pmBOS-ORD
9h 07m1 stop
$129
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Wed, Sep 17 - Sat, Sep 20
JetBlue Logo
10:08 am - 1:37 pmORD-BOS
2h 29mnonstop
JetBlue Logo
7:09 am - 9:22 amBOS-ORD
3h 13mnonstop
$130JetBlue
Find Deal
Sat, Oct 18 - Sat, Oct 25
Spirit Airlines Logo
11:57 am - 11:57 pmORD-BOS
11h 00m1 stop
Spirit Airlines Logo
3:00 pm - 10:48 pmBOS-ORD
8h 48m1 stop
$135Spirit Airlines
Find Deal
Wed, Sep 17 - Tue, Sep 23
Spirit Airlines Logo
11:57 am - 11:57 pmORD-BOS
11h 00m1 stop
Spirit Airlines Logo
3:00 pm - 10:48 pmBOS-ORD
8h 48m1 stop
$136Spirit Airlines
Find Deal
Wed, Sep 17 - Sat, Sep 20
Delta Logo
7:25 am - 10:55 amORD-BOS
2h 30mnonstop
Delta Logo
7:25 am - 9:15 amBOS-ORD
2h 50mnonstop
$137Delta
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Wed, Sep 17 - Sun, Sep 21
Southwest Logo
9:20 pm - 12:40 amMDW-BOS
2h 20mnonstop
Southwest Logo
5:15 am - 6:55 amBOS-MDW
2h 40mnonstop
$137Southwest
Find Deal
Fri, Oct 3 - Tue, Oct 7
American Airlines Logo
5:00 pm - 8:22 pmORD-BOS
2h 22mnonstop
American Airlines Logo
7:14 pm - 9:20 pmBOS-ORD
3h 06mnonstop
$141American Airlines
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Sat, Nov 22 - Mon, Nov 24
Southwest Logo
12:50 pm - 4:05 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
$143Southwest
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Sat, Dec 13 - Wed, Dec 17
Delta Logo
7:10 pm - 10:45 pmORD-BOS
2h 35mnonstop
Delta Logo
4:10 pm - 6:10 pmBOS-ORD
3h 00mnonstop
$155Delta
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Fri, Oct 17 - Wed, Oct 22
American Airlines Logo
7:32 pm - 11:02 pmORD-BOS
2h 30mnonstop
American Airlines Logo
5:24 am - 7:25 amBOS-ORD
3h 01mnonstop
$165American Airlines
Find Deal
Sat, Oct 11 - Mon, Oct 13

Frontier flights from Illinois to Boston

Our best Frontier deals on Illinois to Boston flight tickets
Frontier
Sep 12
ORD6:21 pmChicago O'Hare Intl
12h 22m
1 stop
BOS7:43 amBoston Logan Intl
Sep 15
BOS8:47 amBoston Logan Intl
9h 04m
1 stop
ORD4:51 pmChicago O'Hare Intl
$144
Find similar
Frontier
Sep 5
ORD6:21 pmChicago O'Hare Intl
12h 22m
1 stop
BOS7:43 amBoston Logan Intl
Sep 7
BOS8:47 amBoston Logan Intl
9h 04m
1 stop
ORD4:51 pmChicago O'Hare Intl
$145
Find similar
Frontier
Sep 26
MDW6:21 amChicago Midway
24h 50m
1 stop
BOS8:11 amBoston Logan Intl
Oct 4
BOS8:56 amBoston Logan Intl
28h 48m
1 stop
MDW12:44 pmChicago Midway
$150
Find similar

Southwest flights from Illinois to Boston

Our best Southwest deals on Illinois to Boston flight tickets
Southwest
Oct 3
MDW9:20 pmChicago Midway
2h 20m
BOS12:40 amBoston Logan Intl
Oct 7
BOS5:15 amBoston Logan Intl
2h 40m
MDW6:55 amChicago Midway
$137
Find similar
Southwest
Dec 13
MDW12:50 pmChicago Midway
2h 15m
BOS4:05 pmBoston Logan Intl
Dec 17
BOS5:35 pmBoston Logan Intl
4h 30m
1 stop
MDW9:05 pmChicago Midway
$143
Find similar
Southwest
Sep 19
MDW2:35 pmChicago Midway
7h 25m
1 stop
BOS11:00 pmBoston Logan Intl
Sep 23
BOS3:15 pmBoston Logan Intl
2h 35m
MDW4:50 pmChicago Midway
$147
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Boston that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 28, 2025.
Use the filters below to find and compare flights from Illinois to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/17

11:57 am-11:57 pm

1 stop11h 00m

Boston Logan Intl

Sat 9/20

8:38 am-4:45 pm

1 stop9h 07m

$129

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 10/18

10:08 am-1:37 pm

Nonstop2h 29m

Boston Logan Intl

Sat 10/25

7:09 am-9:22 am

Nonstop3h 13m

$130

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/17

11:57 am-11:57 pm

1 stop11h 00m

Boston Logan Intl

Tue 9/23

3:00 pm-10:48 pm

1 stop8h 48m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/17

11:57 am-11:57 pm

1 stop11h 00m

Boston Logan Intl

Sat 9/20

3:00 pm-10:48 pm

1 stop8h 48m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/17

7:25 am-10:55 am

Nonstop2h 30m

Boston Logan Intl

Sun 9/21

7:25 am-9:15 am

Nonstop2h 50m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 10/3

9:20 pm-12:40 am

Nonstop2h 20m

Boston Logan Intl

Tue 10/7

5:15 am-6:55 am

Nonstop2h 40m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 11/22

5:00 pm-8:22 pm

Nonstop2h 22m

Boston Logan Intl

Mon 11/24

7:14 pm-9:20 pm

Nonstop3h 06m

$141

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 12/13

12:50 pm-4:05 pm

Nonstop2h 15m

Boston Logan Intl

Wed 12/17

5:35 pm-9:05 pm

1 stop4h 30m

$143

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 10/17

7:10 pm-10:45 pm

Nonstop2h 35m

Boston Logan Intl

Wed 10/22

4:10 pm-6:10 pm

Nonstop3h 00m

$155

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 10/11

7:32 pm-11:02 pm

Nonstop2h 30m

Boston Logan Intl

Mon 10/13

5:24 am-7:25 am

Nonstop3h 01m

$165

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Boston from

How to get the cheapest flight ticket from Illinois to Boston

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Boston?

In general, September is the cheapest month to fly from Illinois to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $193. If you aren’t able to travel during the month of September, then book flights to Boston from Illinois during January instead. Flights to Boston in January, while not as cheap as those in September, still average around $217.

What is the cheapest day to depart on your flight to Boston?

The cheapest day to depart from Illinois to Boston is on a Thursday when prices can be found for as low as $241. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Sunday is $304.

What is the cheapest time of day to depart on your flight to Boston?

According to our data, the cheapest time of day to fly to Boston is in the evening. momondo users have found flights departing from Illinois to Boston in the evening for as low as $227. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. At noon is when there is more demand to fly to Boston, so prices are often more expensive at around $288 per ticket.

What is the cheapest Illinois to Boston Logan Intl flight route?

Fly from Chicago Midway to Boston Logan Intl for the best Illinois - Boston Logan Intl flight prices

How far in advance should I book a flight to Boston?

You are more likely to see cheaper flights to Boston from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $230 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Illinois for as low as $188 on momondo.

What cabin class options are available on Illinois to Boston Logan Intl flights?

There are 4 cabin classes available to choose from on Illinois to Boston Logan Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Illinois to Boston flights?

No. A direct flight is the cheapest option for a flight between Illinois to Boston.

Cheap Illinois to Boston flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Boston

Best Price Found

$68

Fastest flight time

2h 15m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in Boston

1 airport
The best one-way flight to Boston from Illinois in the past 72 hours is $68. The best round-trip flight deal from Illinois to Boston found on momondo in the last 72 hours is $99.
The fastest flight from Illinois to Boston takes 2h 15m
Direct flights go from Illinois to Boston on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and Southwest.
There is 1 airport near Boston: Boston Logan Intl (BOS)
Search flight deals

  • When did momondo last update prices for flights from Illinois to Boston Logan Intl Airport?

    Prices for flights from Illinois to Boston Logan Intl Airport were last updated today.

  • How many operators does momondo search for flights from Illinois to Boston Logan Intl Airport?

  • How old do you have to be to fly from Illinois to Boston Logan Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Illinois to Boston Logan Intl Airport.

  • What documentation or ID do you need to fly to Boston Logan Intl Airport?

    The travel and health documents you'll need for your trip to Boston Logan Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Boston Logan Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Illinois to Boston?

Best airlines flying from Illinois to Boston

Compare and see reviews for airlines that fly from Illinois to Boston with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $35Free CancellationRating
6.3
8,028 reviews
Search Spirit Airlines flights
JetBluePriceFrom $77Free CancellationRating
7.2
2,920 reviews
Search JetBlue flights
DeltaPriceFrom $92Free CancellationRating
7.9
7,977 reviews
Search Delta flights
FrontierPriceFrom $100Free CancellationRating
5.8
3,204 reviews
Search Frontier flights
American AirlinesPriceFrom $119Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $128Free CancellationRating
7.4
8,944 reviews
Search United Airlines flights
SouthwestPriceFrom $141Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Hampton Beach
Salem
Ogunquit
Old Orchard Beach
Hampton
York Beach
Plymouth
Kennebunkport
Cambridge
Narragansett
Nashua
South Yarmouth
Gloucester
Brockton
Laconia
Concord
Falmouth
Everett
Wells
Sturbridge

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Boston?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Illinois to Boston. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Illinois to Boston with flexible booking policies on momondo?

momondo does allow users to show only those flights to Boston from Illinois which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Illinois to Boston?

Once all potential Illinois to Boston flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Illinois to Boston right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Boston from Illinois. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Boston trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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