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Cheap flights from Chicago Midway Airport to Boston from $64

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Boston departing on 2/14. 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 Chicago Midway Airport to Boston

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
10:15 am - 1:30 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
2:40 pm - 4:30 pm
BOS
-
MDW
2h 50mnonstop
$127Southwest
Sat, Jan 17 - Sun, Jan 18
Frontier Logo
1:20 pm - 1:03 am
MDW
-
BOS
10h 43m1 stop
Frontier Logo
6:00 am - 12:05 pm
BOS
-
MDW
7h 05m1 stop
$128Frontier
Wed, Jan 21 - Wed, Feb 4
Southwest Logo
9:40 am - 12:55 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
2:40 pm - 4:30 pm
BOS
-
MDW
2h 50mnonstop
$132Southwest
Thu, Jan 15 - Sun, Jan 18
Southwest Logo
10:15 am - 1:30 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:50 am - 11:35 am
BOS
-
MDW
6h 45m1 stop
$137Southwest
Sat, Jan 17 - Sun, Jan 18
Southwest Logo
10:15 am - 1:30 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:50 am - 1:55 pm
BOS
-
MDW
9h 05m2 stops
$142Southwest
Sat, Jan 17 - Sun, Jan 18
Frontier Logo
5:01 pm - 1:13 am
MDW
-
BOS
7h 12m1 stop
Frontier Logo
6:00 am - 12:05 pm
BOS
-
MDW
7h 05m1 stop
$145Frontier
Mon, Jan 26 - Tue, Jan 27
Southwest Logo
2:35 pm - 9:45 pm
MDW
-
BOS
6h 10m1 stop
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
$147Southwest
Wed, Jan 7 - Sat, Jan 17
Southwest Logo
1:50 pm - 9:25 pm
MDW
-
BOS
6h 35m1 stop
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
$152Southwest
Thu, Jan 22 - Thu, Jan 29
Southwest Logo
12:15 pm - 7:25 pm
MDW
-
BOS
6h 10m1 stop
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
$157Southwest
Sat, Jan 17 - Sun, Jan 18
Multiple Airlines Logo
1:00 pm - 11:19 pm
MDW
-
BOS
9h 19m1 stop
Multiple Airlines Logo
7:00 am - 7:52 pm
BOS
-
MDW
13h 52m1 stop
$160Multiple Airlines
Fri, Feb 6 - Sun, Feb 8

Southwest flights from Chicago Midway Airport to Boston

Our best Southwest deals on Chicago Midway Airport to Boston flight tickets
Southwest
Jan 17
MDW10:15 amChicago Midway
2h 15m
BOS1:30 pmBoston Logan Intl
Jan 18
BOS5:30 amBoston Logan Intl
2h 50m
MDW7:20 amChicago Midway
$127
Find similar
Southwest
Jan 15
MDW9:40 amChicago Midway
2h 15m
BOS12:55 pmBoston Logan Intl
Jan 18
BOS2:40 pmBoston Logan Intl
2h 50m
MDW4:30 pmChicago Midway
$132
Find similar
Southwest
Jan 17
MDW10:15 amChicago Midway
2h 15m
BOS1:30 pmBoston Logan Intl
Jan 18
BOS5:50 amBoston Logan Intl
6h 45m
1 stop
MDW11:35 amChicago Midway
$137
Find similar

Frontier flights from Chicago Midway Airport to Boston

Our best Frontier deals on Chicago Midway Airport to Boston flight tickets
Frontier
Jan 21
MDW1:20 pmChicago Midway
10h 43m
1 stop
BOS1:03 amBoston Logan Intl
Feb 4
BOS6:00 amBoston Logan Intl
7h 05m
1 stop
MDW12:05 pmChicago Midway
$128
Find similar
Frontier
Jan 26
MDW5:01 pmChicago Midway
7h 12m
1 stop
BOS1:13 amBoston Logan Intl
Jan 27
BOS6:00 amBoston Logan Intl
7h 05m
1 stop
MDW12:05 pmChicago Midway
$145
Find similar
Frontier
Feb 6
MDW5:01 pmChicago Midway
7h 12m
1 stop
BOS1:13 amBoston Logan Intl
Feb 8
BOS6:00 amBoston Logan Intl
6h 45m
1 stop
MDW11:45 amChicago Midway
$232
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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 December 26, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 1/17

10:15 am-1:30 pm

Nonstop2h 15m

Boston Logan Intl

Sun 1/18

2:40 pm-4:30 pm

Nonstop2h 50m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 1/21

1:20 pm-1:03 am

1 stop10h 43m

Boston Logan Intl

Wed 2/4

6:00 am-12:05 pm

1 stop7h 05m

$128

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 1/15

9:40 am-12:55 pm

Nonstop2h 15m

Boston Logan Intl

Sun 1/18

2:40 pm-4:30 pm

Nonstop2h 50m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 1/17

10:15 am-1:30 pm

Nonstop2h 15m

Boston Logan Intl

Sun 1/18

5:50 am-11:35 am

1 stop6h 45m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 1/17

10:15 am-1:30 pm

Nonstop2h 15m

Boston Logan Intl

Sun 1/18

5:50 am-1:55 pm

2 stops9h 05m

$142

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 1/26

5:01 pm-1:13 am

1 stop7h 12m

Boston Logan Intl

Tue 1/27

6:00 am-12:05 pm

1 stop7h 05m

$145

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 1/7

2:35 pm-9:45 pm

1 stop6h 10m

Boston Logan Intl

Sat 1/17

5:30 am-7:20 am

Nonstop2h 50m

$147

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 1/22

1:50 pm-9:25 pm

1 stop6h 35m

Boston Logan Intl

Thu 1/29

5:30 am-7:20 am

Nonstop2h 50m

$152

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 1/17

12:15 pm-7:25 pm

1 stop6h 10m

Boston Logan Intl

Sun 1/18

5:30 am-7:20 am

Nonstop2h 50m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 2/6

1:00 pm-11:19 pm

1 stop9h 19m

Boston Logan Intl

Sun 2/8

7:00 am-7:52 pm

1 stop13h 52m

$160

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 Chicago Midway Airport 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, January is the cheapest month to fly from Chicago Midway Airport to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $178. If you aren’t able to travel during the month of January, then book flights to Boston from Chicago Midway Airport during March instead. Flights to Boston in March, while not as cheap as those in January, still average around $246.

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

The cheapest day to depart from Chicago Midway Airport to Boston is on a Wednesday when prices can be found for as low as $241. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday is $300.

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 Chicago Midway Airport to Boston in the evening for as low as $216. 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 $296 per ticket.

What is the cheapest Chicago Midway to Boston Logan Intl flight route?

Fly from Chicago Midway to Boston Logan Intl for the best Chicago Midway - 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 Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $281 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago Midway Airport for as low as $192 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway 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.

How have Chicago Midway Airport to Boston flight prices changed over time?

As of December 2025, prices for Chicago Midway Airport to Boston flights are approximately 8% more expensive when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to Boston

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Boston according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Boston (MDW to BOS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Boston

Best Price Found

$98

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Boston

1 airport
The best one-way flight to Boston from Chicago Midway Airport in the past 72 hours is $98. The best round-trip flight deal from Chicago Midway Airport to Boston found on momondo in the last 72 hours is $157.
The fastest flight from Chicago Midway Airport to Boston takes 2h 15m
Direct flights go from Chicago Midway Airport to Boston every day.
There is 1 airport in Boston. From Chicago Midway Airport there are direct flights to Boston Logan Intl (BOS).
Search flight deals

  • How far is Chicago Midway to Boston Logan Intl by plane?

    Chicago Midway and Boston Logan Intl are 854.8 mi apart from one another. Typically, this will take 2h 15m by plane in normal conditions.

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Boston Logan Intl Airport.

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

    The required travel and health documents for your Boston Logan Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Boston Logan Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Boston?

  • What is the most popular airline from Chicago Midway Airport to Boston?

Best airlines flying from Chicago Midway Airport to Boston

Compare and see reviews for airlines that fly from Chicago Midway Airport to Boston with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $135Free CancellationRating
8.0
4,258 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Boston

    Southwest flight deals from Chicago Midway Airport to Boston start from $135 round-trip. Over the 24 Southwest flights for this route in a normal week, average airfare is usually $290 round-trip - but some users have found much cheaper deals with momondo.

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
South Yarmouth
Cambridge
Narragansett
Gloucester
Nashua
Falmouth
Laconia
Brockton
Concord
Sturbridge
Everett
Warwick

Why use momondo?

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

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 Chicago to Boston for you.

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

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

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

Once you have performed a search for Chicago to Boston flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Of course. momondo tracks the price of Chicago to Boston flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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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