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Cheap flights from Chicago Midway Airport to Boston from $59

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 2/18. 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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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
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
$123Southwest
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Thu, Dec 25 - Wed, Dec 31
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
Southwest Logo
5:30 am - 7:15 amBOS-MDW
2h 45mnonstop
$127Southwest
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Wed, Dec 10 - Thu, Dec 11
Southwest Logo
2:25 pm - 5:40 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:20 am - 7:05 amBOS-MDW
2h 45mnonstop
$129Southwest
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Fri, Dec 12 - Sat, Jan 3
Southwest Logo
1:30 pm - 4:45 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:20 am - 7:10 amBOS-MDW
2h 50mnonstop
$132Southwest
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Thu, Dec 11 - Sun, Jan 11
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
Southwest Logo
7:05 pm - 11:55 pmBOS-MDW
5h 50m1 stop
$134Southwest
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Thu, Dec 25 - Sat, Jan 3
Southwest Logo
6:40 am - 12:55 pmMDW-BOS
5h 15m1 stop
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
$137Southwest
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Wed, Dec 10 - Sun, Dec 14
Southwest Logo
2:55 pm - 11:15 pmMDW-BOS
7h 20m1 stop
Southwest Logo
5:20 am - 7:05 amBOS-MDW
2h 45mnonstop
$139Southwest
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Fri, Dec 12 - Sat, Jan 3
Southwest Logo
9:35 am - 12:50 pmMDW-BOS
2h 15mnonstop
Southwest Logo
3:25 pm - 8:40 pmBOS-MDW
6h 15m1 stop
$141Southwest
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Thu, Dec 18 - Thu, Dec 18
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
Southwest Logo
12:20 pm - 7:10 pmBOS-MDW
7h 50m2 stops
$142Southwest
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Mon, Dec 8 - Thu, Dec 11
Southwest Logo
9:35 am - 12:50 pmMDW-BOS
2h 15mnonstop
Southwest Logo
3:25 pm - 8:30 pmBOS-MDW
6h 05m2 stops
$146Southwest
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Thu, Dec 18 - Thu, Dec 18

Southwest flights from Chicago Midway Airport to Boston

Our best Southwest deals on Chicago Midway Airport to Boston flight tickets
Southwest
Dec 25
MDW6:15 pmChicago Midway
2h 20m
BOS9:35 pmBoston Logan Intl
Dec 31
BOS5:35 pmBoston Logan Intl
4h 30m
1 stop
MDW9:05 pmChicago Midway
$123
Find similar
Southwest
Dec 10
MDW6:15 pmChicago Midway
2h 20m
BOS9:35 pmBoston Logan Intl
Dec 11
BOS5:30 amBoston Logan Intl
2h 45m
MDW7:15 amChicago Midway
$127
Find similar
Southwest
Dec 12
MDW2:25 pmChicago Midway
2h 15m
BOS5:40 pmBoston Logan Intl
Jan 3
BOS5:20 amBoston Logan Intl
2h 45m
MDW7:05 amChicago Midway
$129
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Frontier flights from Chicago Midway Airport to Boston

Our best Frontier deals on Chicago Midway Airport to Boston flight tickets
Frontier
Jan 30
MDW5:01 pmChicago Midway
7h 12m
1 stop
BOS1:13 amBoston Logan Intl
Mar 1
BOS6:00 amBoston Logan Intl
18h 25m
1 stop
MDW11:25 pmChicago Midway
$163
Find similar
Frontier
Jan 11
MDW4:21 pmChicago Midway
17h 25m
1 stop
BOS10:46 amBoston Logan Intl
Jan 20
BOS6:00 amBoston Logan Intl
7h 05m
1 stop
MDW12:05 pmChicago Midway
$175
Find similar
Frontier
Dec 24
MDW6:12 amChicago Midway
18h 02m
1 stop
BOS1:14 amBoston Logan Intl
Jan 5
BOS8:08 amBoston Logan Intl
15h 04m
2 stops
MDW10:12 pmChicago Midway
$185
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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 November 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

Thu 12/25

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Wed 12/31

5:35 pm-9:05 pm

1 stop4h 30m

$123

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 12/10

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Thu 12/11

5:30 am-7:15 am

Nonstop2h 45m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/12

2:25 pm-5:40 pm

Nonstop2h 15m

Boston Logan Intl

Sat 1/3

5:20 am-7:05 am

Nonstop2h 45m

$129

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/11

1:30 pm-4:45 pm

Nonstop2h 15m

Boston Logan Intl

Sun 1/11

5:20 am-7:10 am

Nonstop2h 50m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/25

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Sat 1/3

7:05 pm-11:55 pm

1 stop5h 50m

$134

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 12/10

6:40 am-12:55 pm

1 stop5h 15m

Boston Logan Intl

Sun 12/14

5:15 am-7:00 am

Nonstop2h 45m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/12

2:55 pm-11:15 pm

1 stop7h 20m

Boston Logan Intl

Sat 1/3

5:20 am-7:05 am

Nonstop2h 45m

$139

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/18

9:35 am-12:50 pm

Nonstop2h 15m

Boston Logan Intl

Thu 12/18

3:25 pm-8:40 pm

1 stop6h 15m

$141

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 12/8

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Thu 12/11

12:20 pm-7:10 pm

2 stops7h 50m

$142

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/18

9:35 am-12:50 pm

Nonstop2h 15m

Boston Logan Intl

Thu 12/18

3:25 pm-8:30 pm

2 stops6h 05m

$146

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 $198. 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 $237.

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 $239. 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 $302.

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 $219. 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 $302 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 $286 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 November 2025, prices for Chicago Midway Airport to Boston flights are approximately 47% cheaper 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

$65

Fastest flight time

2h 10m

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 $65. The best round-trip flight deal from Chicago Midway Airport to Boston found on momondo in the last 72 hours is $172.
The fastest flight from Chicago Midway Airport to Boston takes 2h 10m
Direct flights go from Chicago Midway Airport to Boston every day.
There is 1 airport near Boston: 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 $137Free CancellationRating
8.0
4,254 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Boston

    Southwest flight deals from Chicago Midway Airport to Boston start from $137 round-trip. Over the 20 Southwest flights for this route in a normal week, average airfare is usually $294 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
Nashua
Gloucester
Falmouth
Laconia
Brockton
Concord
Everett
Sturbridge
Chatham

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

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