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New Hampshire

$69+ Cheap flights from Midway (MDW) to New Hampshire

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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MHT
Aug 24 — Aug 311
Sun 8/24
Sun 8/31
1 adult, Economy
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Cheap flight deals from Midway to New Hampshire

Keep the following information in mind while searching for Midway to New Hampshire flight deals. Data was last updated August 19, 2025.

Round-trip from

$132
(Southwest)

One-way from

$69
(Southwest)

Popular in

April

Cheapest in

September

Average price

$220

Good round-trip deal

$139 or less

Good one-way deal

$105 or less
From Chicago Midway to New Hampshire
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One-way flight from Chicago Midway to New Hampshire
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Highest demand for flights based on searches. 8% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago Midway to New Hampshire.
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Price to beat on a one-way flight from Chicago Midway to New Hampshire.
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Find flight deals from Midway to New Hampshire

Cheapest flights from Midway to New Hampshire
Explore the most affordable flight options available from Midway to New Hampshire. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 19, 2025.

This Southwest deal was found by Cheapflights users on 8/19. 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 9/246:25 amMDW - BOS
1 stop8h 00mSouthwest
Sat 9/275:20 amBOS - MDW
1 stop4h 15mSouthwest
Deal found 8/19$132
This Southwest deal was found by Cheapflights users on 8/18. 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 9/36:25 amMDW - BOS
1 stop8h 00mSouthwest
Fri 9/55:15 amBOS - MDW
Nonstop2h 30mSouthwest
Deal found 8/18$133
This Southwest deal was found by Cheapflights users on 8/18. 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.
Sun 10/126:05 amMDW - BOS
Nonstop2h 15mSouthwest
Fri 10/179:35 pmBOS - MDW
Nonstop2h 40mSouthwest
Deal found 8/18$137
This Southwest deal was found by Cheapflights users on 8/17. 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 9/51:45 pmMDW - BOS
2 stops7h 30mSouthwest
Sun 9/75:30 amBOS - MDW
Nonstop2h 35mSouthwest
Deal found 8/17$142
This Southwest deal was found by Cheapflights users on 8/17. 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 9/36:25 amMDW - BOS
1 stop8h 00mSouthwest
Sun 9/75:30 amBOS - MDW
Nonstop2h 35mSouthwest
Deal found 8/17$143
This Southwest deal was found by Cheapflights users on 8/17. 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 9/1611:45 amMDW - BOS
1 stop4h 20mSouthwest
Tue 9/233:15 pmBOS - MDW
Nonstop2h 35mSouthwest
Deal found 8/17$147
This Southwest deal was found by Cheapflights users on 8/18. 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 12/86:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Tue 12/95:45 amBOS - MDW
2 stops8h 15mSouthwest
Deal found 8/18$152
This Southwest deal was found by Cheapflights users on 8/18. 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 9/246:25 amMDW - BOS
1 stop8h 00mSouthwest
Mon 9/298:20 pmBOS - MDW
Nonstop2h 35mSouthwest
Deal found 8/18$153
This Southwest deal was found by Cheapflights users on 8/19. 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 11/245:00 amMDW - BOS
1 stop6h 50mSouthwest
Thu 11/279:20 amBOS - MDW
1 stop5h 55mSouthwest
Deal found 8/19$157
This FlightHub deal was found by Cheapflights users on 8/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/126:20 amMDW - BOS
1 stop24h 23mFrontier
Sun 9/149:38 amBOS - MDW
1 stop22h 33mFrontier
Deal found 8/18$161
This FlightHub deal was found by Cheapflights users on 8/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/33:03 pmMDW - BOS
1 stop17h 55mFrontier
Fri 9/510:53 amBOS - MDW
1 stop6h 07mFrontier
Deal found 8/18$166
This Southwest deal was found by Cheapflights users on 8/18. 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 10/1811:20 amMDW - PWM
Nonstop2h 10mSouthwest
Wed 10/221:55 pmPWM - MDW
1 stop5h 35mSouthwest
Deal found 8/18$241

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to 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, Cheapflights users made 2,558,603 searches. Data last updated August 19, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to New Hampshire that are best for you.

Fly from

Midway

Fly to

New Hampshire

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 11/7

6:45 am-6:10 pm

1 stop10h 25m

Boston Logan Intl

Mon 11/10

5:55 pm-11:00 pm

1 stop6h 05m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 9/24

6:25 am-3:25 pm

1 stop8h 00m

Boston Logan Intl

Sat 9/27

5:20 am-8:35 am

1 stop4h 15m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 9/3

6:25 am-3:25 pm

1 stop8h 00m

Boston Logan Intl

Fri 9/5

5:15 am-6:45 am

Nonstop2h 30m

$133

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 9/3

6:25 am-3:25 pm

1 stop8h 00m

Boston Logan Intl

Wed 9/3

5:40 pm-7:20 pm

Nonstop2h 40m

$133

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/5

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Sun 12/7

5:15 am-7:00 am

Nonstop2h 45m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/4

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Mon 12/8

5:30 am-7:15 am

Nonstop2h 45m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 10/12

6:05 am-9:20 am

Nonstop2h 15m

Boston Logan Intl

Fri 10/17

9:35 pm-11:15 pm

Nonstop2h 40m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 12/8

1:30 pm-4:45 pm

Nonstop2h 15m

Boston Logan Intl

Tue 12/9

1:35 pm-3:20 pm

Nonstop2h 45m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 10/27

6:05 am-9:20 am

Nonstop2h 15m

Boston Logan Intl

Fri 10/31

4:30 pm-6:15 pm

Nonstop2h 45m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 9/20

5:40 pm-9:00 pm

Nonstop2h 20m

Boston Logan Intl

Tue 9/23

5:40 pm-7:20 pm

Nonstop2h 40m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 44 results
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5

Best time to book a flight from Midway to New Hampshire

Have a flexible travel schedule? Discover the best time to fly to New Hampshire from Midway 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 Chicago Midway Airport to New Hampshire

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

Find hourly flight availability from Midway to New Hampshire. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 19, 2025.

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

Reviews of airlines servicing New Hampshire

Get insights into the airlines that provide service to New Hampshire. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to New Hampshire. Reviews last updated August 19, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to New Hampshire, such as Southwest. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Midway to New Hampshire. 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 Chicago Midway Airport to New Hampshire?

    A quick flight from Chicago Midway Airport to New Hampshire can take about 10h 25m. Southwest provides one of the quickest options available for as low as $132. The distance from Chicago Midway Airport to New Hampshire is about 857 mi.

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

    The most popular route from Chicago Midway Airport to New Hampshire is Chicago Midway - Boston Logan Intl. You may also consider Chicago Midway - Portland or Chicago Midway - Manchester.

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

    On average you can expect to pay $199 for a flight from Chicago Midway Airport to New Hampshire. The cheapest flight overall is $105 while the most popular route, (Chicago Midway - Boston Logan Intl) is currently priced at $107.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to New Hampshire 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 Chicago Midway Airport to New Hampshire?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to New Hampshire (average of $334). Flying from Chicago Midway Airport to New Hampshire in April is currently the most expensive (average of $395). 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.

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Alternative routes for Midway to New Hampshire

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

Discover the top airline that operate flights from Midway to New Hampshire. 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 August 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$197Average$429FlexibilityNo cancel feeOn-time63%

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