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Cheap flights from Boston to Illinois from $55

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Illinois departing on 8/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Boston to Illinois

Cheap round-trip flights

Spirit Airlines Logo
6:05 am - 7:07 pmBOS-ORD
14h 02m1 stop
Spirit Airlines Logo
11:57 am - 11:57 pmORD-BOS
11h 00m1 stop
$112Spirit Airlines
Find Deal
Wed, Sep 3 - Tue, Sep 9
United Airlines Logo
6:10 am - 8:05 amBOS-ORD
2h 55mnonstop
United Airlines Logo
9:15 pm - 12:45 amORD-BOS
2h 30mnonstop
$117United Airlines
Find Deal
Tue, Sep 2 - Thu, Sep 4
Southwest Logo
8:35 am - 10:10 amBOS-MDW
2h 35mnonstop
Southwest Logo
10:00 am - 1:25 pmMDW-BOS
2h 25mnonstop
$127Southwest
Find Deal
Thu, Sep 4 - Sun, Sep 7
JetBlue Logo
7:00 am - 8:56 amBOS-ORD
2h 56mnonstop
JetBlue Logo
9:51 am - 1:20 pmORD-BOS
2h 29mnonstop
$129JetBlue
Find Deal
Sat, Sep 6 - Wed, Sep 10
Southwest Logo
12:20 pm - 1:55 pmBOS-MDW
2h 35mnonstop
Southwest Logo
6:25 am - 3:25 pmMDW-BOS
8h 00m1 stop
$133Southwest
Find Deal
Sat, Aug 30 - Tue, Sep 2
American Airlines Logo
5:00 am - 6:51 amBOS-ORD
2h 51mnonstop
American Airlines Logo
5:36 pm - 9:00 pmORD-BOS
2h 24mnonstop
$136American Airlines
Find Deal
Sat, Sep 13 - Sat, Sep 20
American Airlines Logo
5:00 am - 6:51 amBOS-ORD
2h 51mnonstop
American Airlines Logo
6:05 am - 9:32 amORD-BOS
2h 27mnonstop
$138American Airlines
Find Deal
Sun, Sep 14 - Sun, Sep 21
Delta Logo
7:55 pm - 9:56 pmBOS-ORD
3h 01mnonstop
Delta Logo
10:15 am - 1:48 pmORD-BOS
2h 33mnonstop
$147Delta
Find Deal
Thu, Sep 4 - Sat, Sep 6
JetBlue Logo
2:45 pm - 8:49 pmBOS-ORD
7h 04m1 stop
JetBlue Logo
7:50 pm - 11:25 pmORD-BOS
2h 35mnonstop
$169JetBlue
Find Deal
Fri, Sep 12 - Fri, Sep 19
Delta Logo
7:25 am - 9:15 amBOS-ORD
2h 50mnonstop
Delta Logo
6:59 pm - 10:40 pmORD-BOS
2h 41mnonstop
$173Delta
Find Deal
Thu, Oct 2 - Fri, Oct 3

JetBlue flights from Boston to Illinois

Our best JetBlue deals on Boston to Illinois flight tickets
JetBlue
Sep 6
BOS7:00 amBoston Logan Intl
2h 56m
ORD8:56 amChicago O'Hare Intl
Sep 10
ORD9:51 amChicago O'Hare Intl
2h 29m
BOS1:20 pmBoston Logan Intl
$129
Find similar
JetBlue
Aug 5
BOS6:00 amBoston Logan Intl
2h 55m
ORD7:55 amChicago O'Hare Intl
Aug 14
ORD8:40 amChicago O'Hare Intl
2h 24m
BOS12:04 pmBoston Logan Intl
$137
Find similar
JetBlue
Sep 12
BOS2:45 pmBoston Logan Intl
7h 04m
1 stop
ORD8:49 pmChicago O'Hare Intl
Sep 19
ORD7:50 pmChicago O'Hare Intl
2h 35m
BOS11:25 pmBoston Logan Intl
$169
Find similar

Spirit Airlines flights from Boston to Illinois

Our best Spirit Airlines deals on Boston to Illinois flight tickets
Spirit Airlines
Sep 3
BOS6:05 amBoston Logan Intl
14h 02m
1 stop
ORD7:07 pmChicago O'Hare Intl
Sep 9
ORD11:57 amChicago O'Hare Intl
11h 00m
1 stop
BOS11:57 pmBoston Logan Intl
$112
Find similar
Spirit Airlines
Aug 20
BOS6:05 amBoston Logan Intl
14h 02m
1 stop
ORD7:07 pmChicago O'Hare Intl
Aug 26
ORD8:12 pmChicago O'Hare Intl
14h 06m
1 stop
BOS11:18 amBoston Logan Intl
$121
Find similar
Spirit Airlines
Sep 9
BOS12:20 pmBoston Logan Intl
10h 38m
1 stop
ORD9:58 pmChicago O'Hare Intl
Sep 16
ORD11:57 amChicago O'Hare Intl
11h 00m
1 stop
BOS11:57 pmBoston Logan Intl
$124
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Boston to Illinois 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 July 31, 2025.
Use the filters below to find and compare flights from Boston to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 9/3

6:05 am-7:07 pm

1 stop14h 02m

Chicago O'Hare Intl

Tue 9/9

11:57 am-11:57 pm

1 stop11h 00m

$112

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/2

6:10 am-8:05 am

Nonstop2h 55m

Chicago O'Hare Intl

Thu 9/4

9:15 pm-12:45 am

Nonstop2h 30m

$117

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/4

8:35 am-10:10 am

Nonstop2h 35m

Chicago Midway

Sun 9/7

10:00 am-1:25 pm

Nonstop2h 25m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/6

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 9/10

9:51 am-1:20 pm

Nonstop2h 29m

$129

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 8/30

12:20 pm-1:55 pm

Nonstop2h 35m

Chicago Midway

Tue 9/2

6:25 am-3:25 pm

1 stop8h 00m

$133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/13

5:00 am-6:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Sat 9/20

5:36 pm-9:00 pm

Nonstop2h 24m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 9/14

5:00 am-6:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Sun 9/21

6:05 am-9:32 am

Nonstop2h 27m

$138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

7:55 pm-9:56 pm

Nonstop3h 01m

Chicago O'Hare Intl

Sat 9/6

10:15 am-1:48 pm

Nonstop2h 33m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 9/12

2:45 pm-8:49 pm

1 stop7h 04m

Chicago O'Hare Intl

Fri 9/19

7:50 pm-11:25 pm

Nonstop2h 35m

$169

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/2

7:25 am-9:15 am

Nonstop2h 50m

Chicago O'Hare Intl

Fri 10/3

6:59 pm-10:40 pm

Nonstop2h 41m

$173

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 Illinois from

How to get the cheapest flight ticket from Boston to Illinois

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 Illinois?

The cheapest month to fly to Illinois from Boston is in September. Flight prices, which tend to average around $177, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of September, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $194.

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

The cheapest day to depart from Boston to Illinois is on a Friday when prices can be found for as low as $312. Flights from Boston to Illinois on a Sunday will generally be more expensive and average around $421. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our most recent data shows that the best time of day to fly to Illinois is in the evening. Flights from Boston to Illinois during this time can be as low as $268. Flights in the afternoon are often more expensive with an average ticket price of $350.

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

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

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

You are more likely to see cheaper flights to Illinois from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $243 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Boston for as low as $211 on momondo.

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

There are 4 cabin classes available to choose from on Boston Logan Intl to Illinois 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 Boston to Illinois flights?

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

Cheap Boston to Illinois flight deals and tips

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

Best Price Found

$55

Fastest flight time

2h 30m

Direct flights

Every day

Airports in Illinois

5 airports
The best one-way flight to Illinois from Boston in the past 72 hours is $55. The best round-trip flight deal from Boston to Illinois found on momondo in the last 72 hours is $112.
The fastest flight from Boston to Illinois takes 2h 30m
Direct flights go from Boston to Illinois every day.
There are 5 airports near Illinois: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Greater Peoria (PIA), Lambert-St Louis (STL), Champaign University-Willard (CMI)
Search flight deals

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

    Prices for flights from Boston Logan Intl Airport to Illinois are refreshed on a daily basis.

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

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

    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 Boston Logan Intl Airport to Illinois.

  • What documentation or ID do you need to fly to Illinois?

    The necessary travel and health documents for your Illinois trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Boston to Illinois

Compare and see reviews for airlines that fly from Boston to Illinois with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $37Free CancellationRating
6.3
8,048 reviews
Search Spirit Airlines flights
JetBluePriceFrom $74Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
DeltaPriceFrom $94Free CancellationRating
8.0
7,981 reviews
Search Delta flights
United AirlinesPriceFrom $97Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
FrontierPriceFrom $100Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
SouthwestPriceFrom $125Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
American AirlinesPriceFrom $136Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Boston to Illinois for you.

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

All flight searches from Boston to Illinois on momondo can be filtered to show those which offer flexible booking policies.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Boston to Illinois.

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

Price alerts on flights to Illinois from Boston are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Illinois trip

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