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$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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
MHT — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap 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 September 16, 2025.

Round-trip from

$123
(Southwest)

One-way from

$64
(Southwest)

Popular in

March

Cheapest in

January

Average price

$199

Good round-trip deal

$342 or less

Good one-way deal

$187 or less
From New Hampshire to Chicago Midway
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One-way flight from New Hampshire to Chicago Midway
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Highest demand for flights based on searches. 6% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from New Hampshire to Chicago Midway.
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Price to beat on a one-way flight from New Hampshire to Chicago Midway.
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Find 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 September 16, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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 11/115:35 pmBOS - MDW
1 stop4h 30mSouthwest
Fri 11/147:15 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/15$123
This Southwest deal was found by Cheapflights users on 9/15. 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 10/25:35 amBOS - MDW
1 stop5h 40mSouthwest
Mon 10/66:05 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/15$127
This Southwest deal was found by Cheapflights users on 9/15. 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 10/305:15 amBOS - MDW
Nonstop2h 40mSouthwest
Sun 11/25:45 amMDW - BOS
1 stop10h 25mSouthwest
Deal found 9/15$133
This Southwest deal was found by Cheapflights users on 9/15. 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 11/146:50 pmBOS - MDW
1 stop5h 40mSouthwest
Sun 11/165:00 amMDW - BOS
1 stop6h 50mSouthwest
Deal found 9/15$137
This Southwest deal was found by Cheapflights users on 9/15. 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 11/45:35 pmBOS - MDW
1 stop4h 30mSouthwest
Fri 11/79:30 amMDW - BOS
2 stops7h 45mSouthwest
Deal found 9/15$138
This Southwest deal was found by Cheapflights users on 9/15. 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 10/307:15 amBOS - MDW
2 stops7h 05mSouthwest
Tue 11/49:20 amMDW - BOS
1 stop6h 15mSouthwest
Deal found 9/15$142
This Southwest deal was found by Cheapflights users on 9/15. 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 12/35:35 pmBOS - MDW
1 stop4h 30mSouthwest
Sun 12/79:35 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/15$143
This Southwest deal was found by Cheapflights users on 9/16. 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.
Sat 11/225:25 amBOS - MDW
Nonstop2h 45mSouthwest
Fri 11/285:00 amMDW - BOS
1 stop6h 50mSouthwest
Deal found 9/16$147
This Southwest deal was found by Cheapflights users on 9/14. 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.
Sat 11/225:25 amBOS - MDW
Nonstop2h 45mSouthwest
Wed 12/38:25 amMDW - BOS
2 stops7h 10mSouthwest
Deal found 9/14$152
This Southwest deal was found by Cheapflights users on 9/16. 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 9/258:35 amBOS - MDW
Nonstop2h 35mSouthwest
Mon 9/298:35 pmMDW - BOS
1 stop10h 35mSouthwest
Deal found 9/16$153
This Southwest deal was found by Cheapflights users on 9/15. 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.
Sat 11/14:45 pmPWM - MDW
Nonstop2h 35mSouthwest
Tue 11/46:40 amMDW - PWM
1 stop4h 30mSouthwest
Deal found 9/15$241
This Southwest deal was found by Cheapflights users on 9/15. 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 10/285:25 pmPWM - MDW
1 stop4h 25mSouthwest
Fri 10/3112:50 pmMDW - PWM
Nonstop2h 10mSouthwest
Deal found 9/15$244

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 September 16, 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 10/25

10:30 am-12:10 pm

Nonstop2h 40m

Chicago Midway

Tue 10/28

6:10 am-1:15 pm

1 stop6h 05m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/2

5:35 am-10:15 am

1 stop5h 40m

Chicago Midway

Mon 10/6

5:50 pm-9:05 pm

Nonstop2h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/31

5:15 am-10:40 am

1 stop6h 25m

Chicago Midway

Mon 11/3

6:40 am-12:55 pm

1 stop5h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 12/5

1:35 pm-3:20 pm

Nonstop2h 45m

Chicago Midway

Sun 12/7

7:15 pm-10:30 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 11/22

5:25 am-7:10 am

Nonstop2h 45m

Chicago Midway

Fri 11/28

2:55 pm-11:15 pm

1 stop7h 20m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/8

5:30 pm-10:05 pm

1 stop5h 35m

Chicago Midway

Sun 1/11

9:40 am-12:55 pm

Nonstop2h 15m

$147

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 10/28

5:42 am-12:28 pm

2 stops7h 46m

Chicago Midway

Fri 10/31

1:08 pm-12:05 am

2 stops9h 57m

$264

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 10/31

12:45 pm-5:55 pm

1 stop6h 10m

Chicago Midway

Sun 11/2

9:35 am-4:03 pm

1 stop5h 28m

$278

ManchesterChicago

MHT - MDW

MHTMDW

Manchester

Tue 10/21

5:45 pm-7:20 pm

Nonstop2h 35m

Chicago Midway

Wed 10/22

12:00 pm-3:05 pm

Nonstop2h 05m

$297

ManchesterChicago

MHT - MDW

MHTMDW

Manchester

Wed 10/8

5:45 pm-7:20 pm

Nonstop2h 35m

Chicago Midway

Wed 10/15

12:00 pm-3:05 pm

Nonstop2h 05m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 52 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, April is the cheapest month in which you can book a flight from New Hampshire to Chicago Midway Airport (average of $160). Flying from New Hampshire to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from New Hampshire to Chicago Midway Airport as you normally would.

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 $127, Southwest can have you in Chicago Midway Airport from New Hampshire in 2h 40m. 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, Portland - Chicago Midway or Manchester - 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 $341, our data shows the cheapest flight currently is $87. When looking at the most popular route, (Boston Logan Intl - Chicago Midway), you can expect to pay $117 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, April is the cheapest month in which you can book a flight from New Hampshire to Chicago Midway Airport (average of $160). Flying from New Hampshire to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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.
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
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Dallas/Fort Worth to O'Hare Intl flights
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San Francisco to O'Hare Intl flights
Seattle to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Boston to O'Hare Intl flights
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Dulles Intl to O'Hare Intl flights
Denver to O'Hare Intl flights
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John F Kennedy Intl to Midway flights
Santa Ana to O'Hare Intl flights
Baltimore to Midway flights
LaGuardia to Midway flights
Atlanta to Midway flights
Newark to Midway flights
Los Angeles to Midway flights
Dulles Intl to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Austin to O'Hare Intl flights
San Francisco to Midway flights
Raleigh to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Philadelphia to Midway flights
Minneapolis to O'Hare Intl flights
Hobby to Midway flights
Portland to O'Hare Intl flights
Burbank to O'Hare Intl flights
Hobby to O'Hare Intl flights
Providence to O'Hare Intl flights
Seattle to Midway flights
Reagan-National to Midway flights
Miami to O'Hare Intl flights
Hartford to O'Hare Intl flights
Denver to Midway flights
Cleveland to O'Hare Intl flights
Love Field to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
San Jose to O'Hare Intl flights
Minneapolis to Midway flights
San Diego to O'Hare Intl flights
Boston to Midway flights
Orlando to O'Hare Intl flights

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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$196Average$426FlexibilityNo cancel feeOn-time63%

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