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Cheap flights from Chicago Midway Airport to Boston from $145

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 12/2. 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 (MDW-MHT)

Cheap round-trip flights

Southwest Logo
12:50 pm - 3:50 pmMDW-MHT
2h 00mnonstop
Southwest Logo
5:00 am - 6:35 amMHT-MDW
2h 35mnonstop
$299Southwest
Find Deal
Sat, Oct 25 - Tue, Oct 28
Southwest Logo
6:00 am - 12:15 pmMDW-MHT
5h 15m1 stop
Southwest Logo
5:45 pm - 7:20 pmMHT-MDW
2h 35mnonstop
$309Southwest
Find Deal
Sat, Oct 4 - Tue, Oct 7
Southwest Logo
2:35 pm - 9:55 pmMDW-MHT
6h 20m2 stops
Southwest Logo
5:45 pm - 7:20 pmMHT-MDW
2h 35mnonstop
$314Southwest
Find Deal
Sat, Oct 4 - Tue, Oct 7
Southwest Logo
3:25 pm - 9:55 pmMDW-MHT
5h 30m2 stops
Southwest Logo
5:50 am - 12:00 pmMHT-MDW
7h 10m1 stop
$324Southwest
Find Deal
Sat, Oct 4 - Tue, Oct 7
Southwest Logo
3:25 pm - 9:55 pmMDW-MHT
5h 30m2 stops
Southwest Logo
3:50 pm - 10:05 pmMHT-MDW
7h 15m2 stops
$339Southwest
Find Deal
Sat, Oct 4 - Tue, Oct 7
Southwest Logo
8:35 pm - 11:40 pmMDW-MHT
2h 05mnonstop
Southwest Logo
5:00 am - 6:35 amMHT-MDW
2h 35mnonstop
$374Southwest
Find Deal
Fri, Oct 10 - Tue, Oct 14
Southwest Logo
12:00 pm - 3:05 pmMDW-MHT
2h 05mnonstop
Southwest Logo
5:05 pm - 10:20 pmMHT-MDW
6h 15m1 stop
$384Southwest
Find Deal
Wed, Oct 22 - Fri, Oct 24
Southwest Logo
7:35 am - 5:00 pmMDW-MHT
8h 25m2 stops
Southwest Logo
7:10 pm - 8:45 pmMHT-MDW
2h 35mnonstop
$389Southwest
Find Deal
Wed, Oct 22 - Fri, Oct 24
Southwest Logo
5:20 pm - 12:20 amMDW-MHT
6h 00m1 stop
Southwest Logo
7:10 pm - 8:45 pmMHT-MDW
2h 35mnonstop
$394Southwest
Find Deal
Fri, Oct 24 - Mon, Oct 27
Southwest Logo
8:35 pm - 11:40 pmMDW-MHT
2h 05mnonstop
Southwest Logo
5:50 am - 12:05 pmMHT-MDW
7h 15m2 stops
$399Southwest
Find Deal
Fri, Oct 10 - Tue, Oct 14

Southwest flights from Chicago Midway Airport to Manchester, New Hampshire

Our best Southwest deals on Chicago Midway Airport to Manchester, New Hampshire flight tickets
Southwest
Oct 25
MDW12:50 pmChicago Midway
2h 00m
MHT3:50 pmManchester
Oct 28
MHT5:00 amManchester
2h 35m
MDW6:35 amChicago Midway
$299
Find similar
Southwest
Oct 4
MDW6:00 amChicago Midway
5h 15m
1 stop
MHT12:15 pmManchester
Oct 7
MHT5:45 pmManchester
2h 35m
MDW7:20 pmChicago Midway
$309
Find similar
Southwest
Oct 4
MDW2:35 pmChicago Midway
6h 20m
2 stops
MHT9:55 pmManchester
Oct 7
MHT5:45 pmManchester
2h 35m
MDW7:20 pmChicago Midway
$314
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Manchester, New Hampshire 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 September 4, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Manchester, New Hampshire that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Sat 10/25

12:50 pm-3:50 pm

Nonstop2h 00m

Manchester

Tue 10/28

5:00 am-6:35 am

Nonstop2h 35m

$299

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Sat 10/4

6:00 am-12:15 pm

1 stop5h 15m

Manchester

Tue 10/7

5:45 pm-7:20 pm

Nonstop2h 35m

$309

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Sat 10/4

2:35 pm-9:55 pm

2 stops6h 20m

Manchester

Tue 10/7

5:45 pm-7:20 pm

Nonstop2h 35m

$314

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Sat 10/4

3:25 pm-9:55 pm

2 stops5h 30m

Manchester

Tue 10/7

5:50 am-12:00 pm

1 stop7h 10m

$324

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Sat 10/4

3:25 pm-9:55 pm

2 stops5h 30m

Manchester

Tue 10/7

3:50 pm-10:05 pm

2 stops7h 15m

$339

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Fri 10/10

8:35 pm-11:40 pm

Nonstop2h 05m

Manchester

Tue 10/14

5:00 am-6:35 am

Nonstop2h 35m

$374

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Wed 10/22

12:00 pm-3:05 pm

Nonstop2h 05m

Manchester

Fri 10/24

5:05 pm-10:20 pm

1 stop6h 15m

$384

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Wed 10/22

7:35 am-5:00 pm

2 stops8h 25m

Manchester

Fri 10/24

7:10 pm-8:45 pm

Nonstop2h 35m

$389

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Fri 10/24

5:20 pm-12:20 am

1 stop6h 00m

Manchester

Mon 10/27

7:10 pm-8:45 pm

Nonstop2h 35m

$394

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Fri 10/10

8:35 pm-11:40 pm

Nonstop2h 05m

Manchester

Tue 10/14

5:50 am-12:05 pm

2 stops7h 15m

$399

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 Manchester, New Hampshire

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 day to depart on your flight to Manchester, New Hampshire?

Our data shows that Tuesday is the least expensive day to fly to Manchester, New Hampshire. Tickets to fly out on this day can be as low as $356. 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 Manchester, New Hampshire on Sunday is $437.

What is the cheapest time of day to depart on your flight to Manchester, New Hampshire?

Our most recent data shows that the best time of day to fly to Manchester, New Hampshire is in the evening. Flights from Chicago Midway Airport to Manchester, New Hampshire during this time can be as low as $338. Flights at noon are often more expensive with an average ticket price of $429.

What is the cheapest Chicago Midway to Manchester flight route?

Fly from Chicago Midway to Manchester for the best Chicago Midway - Manchester flight prices

What cabin class options are available on Chicago Midway to Manchester flights?

There is only 1 cabin class available to choose from on Chicago Midway to Manchester flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from Chicago Midway Airport to Manchester, New Hampshire

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

Cheap Chicago Midway Airport to Manchester, New Hampshire (MDW to MHT) flight deals and tips

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

Best Price Found

$148

Fastest flight time

2h 00m

Direct flights

Every day

Airports in Manchester, New Hampshire

1 airport
The best one-way flight to Manchester, New Hampshire from Chicago Midway Airport in the past 72 hours is $148. The best round-trip flight deal from Chicago Midway Airport to Manchester, New Hampshire found on momondo in the last 72 hours is $139.
The fastest flight from Chicago Midway Airport to Manchester, New Hampshire takes 2h 00m
Direct flights go from Chicago Midway Airport to Manchester, New Hampshire every day.
There is 1 airport near Manchester, New Hampshire: Manchester (MHT)
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  • How far is Chicago Midway to Manchester by plane?

    Manchester is 833.6 mi away from Chicago Midway. In terms of flight time, this usually takes a little over 2h 00m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Manchester Airport?

    Prices for flights from Chicago Midway Airport to Manchester Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Manchester Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Manchester Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Manchester Airport.

  • What documentation or ID do you need to fly to Manchester Airport?

    The necessary travel and health documents for your Manchester Airport 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 Chicago Midway Airport to Manchester, New Hampshire?

  • What is the most popular airline from Chicago Midway Airport to Manchester, New Hampshire?

Best airlines flying from Chicago Midway Airport to Manchester, New Hampshire

Compare and see reviews for airlines that fly from Chicago Midway Airport to Manchester, New Hampshire with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $197Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Manchester, New Hampshire

    Across 10 Southwest flights from Chicago Midway Airport to Manchester, New Hampshire this week, the average price was $430, with the best Southwest deals starting from $197 round-trip. 4,242 users have rated Southwest on momondo, with an average score of 8.0/10.

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
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Why use momondo?

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

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 Manchester for you.

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

Flights from Chicago to Manchester with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

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 Chicago to Manchester.

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

Yes. momondo can track prices for Chicago to Manchester flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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