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Midway

$64+ Cheap flights from New Hampshire to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
MHT — MDW
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from New Hampshire to Midway

Cheapest flights from New Hampshire to Midway
Explore the most affordable flight options available from New Hampshire to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Southwest deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Tue 1/62:35 pmMDW - BOS
1 stop6h 10mSouthwest
Deal found 12/21$212
This Southwest deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Fri 1/211:45 amMDW - BOS
1 stop6h 50mSouthwest
Deal found 12/21$242
This Southwest deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Thu 1/16:35 amMDW - BOS
1 stop5h 55mSouthwest
Deal found 12/22$266
This Expedia deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:03 amBOS - MDW
1 stop7h 35mFrontier
Wed 12/313:10 pmMDW - BOS
1 stop17h 42mFrontier
Deal found 12/22$293
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:09 amBOS - MDW
1 stop12h 03mFrontier
Mon 1/53:10 pmMDW - BOS
2 stops33h 09mFrontier
Deal found 12/22$295
This Southwest deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:20 pmBOS - MDW
1 stop6h 30mSouthwest
Fri 1/29:40 pmMDW - BOS
1 stop9h 35mSouthwest
Deal found 12/22$302
This Southwest deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:30 pmPWM - MDW
1 stop4h 25mSouthwest
Tue 12/305:45 amMDW - PWM
1 stop4h 25mSouthwest
Deal found 12/22$494
This Southwest deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2412:55 pmMHT - MDW
1 stop5h 55mSouthwest
Thu 12/259:20 amMDW - MHT
1 stop6h 15mSouthwest
Deal found 12/21$581
This Southwest deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:40 amMHT - MDW
1 stop4h 20mSouthwest
Thu 1/19:20 amMDW - MHT
1 stop6h 15mSouthwest
Deal found 12/21$648
This Southwest deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:40 amMHT - MDW
1 stop4h 20mSouthwest
Sun 12/288:15 pmMDW - MHT
1 stop13h 30mSouthwest
Deal found 12/22$737
This Delta deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/285:45 amPWM - MDW
1 stop7h 13mDelta
Tue 12/309:29 amMDW - PWM
1 stop5h 39mDelta
Deal found 12/22$744
This Southwest deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:30 pmPWM - MDW
1 stop6h 35mSouthwest
Sun 12/285:45 amMDW - PWM
1 stop4h 25mSouthwest
Deal found 12/22$759

Find flight deals from New Hampshire to Midway

Keep the following information in mind while searching for New Hampshire to Midway flight deals. Data was last updated December 23, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$128
(Frontier)

One-way from

$64
(Southwest)

Popular in

April

Cheapest in

September

Average price

$257

Good round-trip deal

$405 or less

Good one-way deal

$192 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
Search Deals
From New Hampshire to Chicago Midway
Search Deals
One-way flight from New Hampshire to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from New Hampshire to Chicago Midway.
Search Deals
Price to beat on a one-way flight from New Hampshire to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from New Hampshire to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated December 23, 2025.
Use the filters below to find and compare flights from New Hampshire to Chicago Midway Airport that are best for you.

Fly from

New Hampshire

Fly to

Midway

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/10

7:10 am-11:35 am

1 stop5h 25m

Chicago Midway

Thu 1/15

6:35 pm-9:50 pm

Nonstop2h 15m

$141

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 1/26

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Tue 1/27

1:50 pm-9:25 pm

1 stop6h 35m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 2/24

5:50 am-11:35 am

1 stop6h 45m

Chicago Midway

Fri 2/27

6:05 am-9:25 am

Nonstop2h 20m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/17

7:10 am-11:35 am

1 stop5h 25m

Chicago Midway

Tue 1/20

2:35 pm-9:45 pm

1 stop6h 10m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 1/14

2:40 pm-4:30 pm

Nonstop2h 50m

Chicago Midway

Wed 1/21

2:00 pm-5:10 pm

Nonstop2h 10m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 3/9

6:25 pm-8:25 pm

Nonstop3h 00m

Chicago Midway

Thu 3/12

7:55 am-11:10 am

Nonstop2h 15m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 1/26

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Mon 2/2

2:00 pm-5:10 pm

Nonstop2h 10m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/9

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sun 1/11

12:30 pm-10:10 pm

1 stop8h 40m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 2/9

5:20 am-7:10 am

Nonstop2h 50m

Chicago Midway

Tue 2/10

2:00 pm-5:10 pm

Nonstop2h 10m

$162

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 2/12

9:00 am-1:50 pm

1 stop5h 50m

Chicago Midway

Sat 2/14

6:10 pm-9:25 pm

Nonstop2h 15m

$162

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 48 results
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Best time to book a flight from New Hampshire to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from New Hampshire with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from New Hampshire to Chicago Midway Airport

What is the cheapest month to book a flight from New Hampshire to Chicago Midway Airport?

Currently, September is the cheapest month in which you can book a flight from New Hampshire to Chicago Midway Airport (average of $180). Flying from New Hampshire to Chicago Midway Airport in December is currently the most expensive (average of $402). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from NH to MDW?

Find hourly flight availability from New Hampshire to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

When flying from New Hampshire to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 33% versus a flight at noon.

Related info for your journey

Find useful and relevant information for your journey from New Hampshire to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from New Hampshire to Chicago Midway Airport?

    For as low as $141, Southwest can have you in Chicago Midway Airport from New Hampshire in 5h 25m. The distance between New Hampshire and Chicago Midway Airport is about 857 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from New Hampshire to Chicago Midway Airport?

    Most travelers choose Boston Logan Intl - Chicago Midway, Manchester - Chicago Midway or Portland - Chicago Midway when deciding on the best route from New Hampshire to Chicago Midway Airport.

  • What are the cheapest flights from New Hampshire to Chicago Midway Airport?

    While on average a flight from New Hampshire to Chicago Midway Airport is generally $351, our data shows the cheapest flight currently is $133. When looking at the most popular route, (Boston Logan Intl - Chicago Midway), you can expect to pay $137 for that flight.

  • Can I find deals for flights from New Hampshire to Midway that include hotel bookings?

    Yes. In addition to deals on New Hampshire to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from New Hampshire to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New Hampshire to Midway.

  • Can I find deals for business class flights from New Hampshire to Midway?

    Yes. Cheapflights offers flight deals from New Hampshire to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New Hampshire to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from New Hampshire to Chicago Midway Airport (average of $180). Flying from New Hampshire to Chicago Midway Airport in December is currently the most expensive (average of $402). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for New Hampshire to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from New Hampshire to Midway

Discover the top airline that operate flights from New Hampshire to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$196Average$431FlexibilityNo cancel feeOn-time63%

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