Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Boston from $103

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 10/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to Boston

Cheap round-trip flights

Southwest Logo
12:30 pm - 8:40 pmMDW-MHT
7h 10m1 stop
Southwest Logo
5:45 pm - 7:20 pmMHT-MDW
2h 35mnonstop
$307Southwest
Find Deal
Wed, Oct 8 - Wed, Oct 15
Southwest Logo
12:30 pm - 8:40 pmMDW-MHT
7h 10m1 stop
Southwest Logo
5:50 am - 12:00 pmMHT-MDW
7h 10m1 stop
$317Southwest
Find Deal
Wed, Oct 8 - Wed, Oct 15
Southwest Logo
8:35 pm - 11:40 pmMDW-MHT
2h 05mnonstop
Southwest Logo
1:15 pm - 7:40 pmMHT-MDW
7h 25m2 stops
$322Southwest
Find Deal
Mon, Oct 27 - Wed, Oct 29
Southwest Logo
4:45 pm - 7:50 pmMDW-MHT
2h 05mnonstop
Southwest Logo
5:00 am - 6:30 amMHT-MDW
2h 30mnonstop
$326Southwest
Find Deal
Fri, Oct 31 - Fri, Nov 7
Southwest Logo
8:35 pm - 11:40 pmMDW-MHT
2h 05mnonstop
Southwest Logo
8:40 am - 2:20 pmMHT-MDW
6h 40m1 stop
$327Southwest
Find Deal
Thu, Oct 16 - Mon, Oct 20
Southwest Logo
8:35 pm - 11:40 pmMDW-MHT
2h 05mnonstop
Southwest Logo
5:30 am - 12:20 pmMHT-MDW
7h 50m2 stops
$332Southwest
Find Deal
Thu, Oct 23 - Sat, Oct 25
Southwest Logo
11:30 am - 4:25 pmMDW-MHT
3h 55m1 stop
Southwest Logo
5:00 am - 6:30 amMHT-MDW
2h 30mnonstop
$336Southwest
Find Deal
Fri, Oct 31 - Fri, Nov 7
Southwest Logo
5:20 pm - 12:20 amMDW-MHT
6h 00m1 stop
Southwest Logo
8:40 am - 2:20 pmMHT-MDW
6h 40m1 stop
$337Southwest
Find Deal
Thu, Oct 16 - Mon, Oct 20
Logo
8:05 am - 6:56 pmMDW-MHT
9h 51m2 stops
Logo
7:36 pm - 10:57 amMHT-MDW
16h 21m1 stop
$378
Find Deal
Wed, Oct 22 - Sat, Oct 25
Logo
8:35 am - 6:56 pmMDW-MHT
9h 21m1 stop
Logo
9:59 am - 10:21 amMHT-MDW
25h 22m2 stops
$487
Find Deal
Sat, Oct 11 - Fri, Oct 17

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 8
MDW12:30 pmChicago Midway
7h 10m
1 stop
MHT8:40 pmManchester
Oct 15
MHT5:45 pmManchester
2h 35m
MDW7:20 pmChicago Midway
$307
Find similar
Southwest
Oct 8
MDW12:30 pmChicago Midway
7h 10m
1 stop
MHT8:40 pmManchester
Oct 15
MHT5:50 amManchester
7h 10m
1 stop
MDW12:00 pmChicago Midway
$317
Find similar
Southwest
Oct 27
MDW8:35 pmChicago Midway
2h 05m
MHT11:40 pmManchester
Oct 29
MHT1:15 pmManchester
7h 25m
2 stops
MDW7:40 pmChicago Midway
$322
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 15, 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

Wed 10/8

12:30 pm-8:40 pm

1 stop7h 10m

Manchester

Wed 10/15

5:45 pm-7:20 pm

Nonstop2h 35m

$307

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Wed 10/8

12:30 pm-8:40 pm

1 stop7h 10m

Manchester

Wed 10/15

5:50 am-12:00 pm

1 stop7h 10m

$317

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Mon 10/27

8:35 pm-11:40 pm

Nonstop2h 05m

Manchester

Wed 10/29

1:15 pm-7:40 pm

2 stops7h 25m

$322

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Fri 10/31

4:45 pm-7:50 pm

Nonstop2h 05m

Manchester

Fri 11/7

5:00 am-6:30 am

Nonstop2h 30m

$326

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Thu 10/16

8:35 pm-11:40 pm

Nonstop2h 05m

Manchester

Mon 10/20

8:40 am-2:20 pm

1 stop6h 40m

$327

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Thu 10/23

8:35 pm-11:40 pm

Nonstop2h 05m

Manchester

Sat 10/25

5:30 am-12:20 pm

2 stops7h 50m

$332

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Fri 10/31

11:30 am-4:25 pm

1 stop3h 55m

Manchester

Fri 11/7

5:00 am-6:30 am

Nonstop2h 30m

$336

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Thu 10/16

5:20 pm-12:20 am

1 stop6h 00m

Manchester

Mon 10/20

8:40 am-2:20 pm

1 stop6h 40m

$337

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Wed 10/22

8:05 am-6:56 pm

2 stops9h 51m

Manchester

Sat 10/25

7:36 pm-10:57 am

1 stop16h 21m

$378

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Sat 10/11

8:35 am-6:56 pm

1 stop9h 21m

Manchester

Fri 10/17

9:59 am-10:21 am

2 stops25h 22m

$487

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 Thursday as prices are generally higher than usual. According to our data, the average ticket price to Manchester, New Hampshire on Thursday is $438.

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 $432.

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

Fastest flight time

2h 00m

Direct flights

Every day

Airports in Manchester, New Hampshire

1 airport
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)
Search flight deals

  • 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 05m.

  • 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 9 Southwest flights from Chicago Midway Airport to Manchester, New Hampshire this week, the average price was $429, 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
Keene

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.

An easier way to manage your Manchester, New Hampshire 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 10/15
Wed 10/22
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States