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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 12/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MHT
Nov 8 — Nov 151
Sat 11/8
Sat 11/15
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 October 9, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$124
(Kiwi.com)

One-way from

$69
(Southwest)

Popular in

April

Cheapest in

September

Average price

$241

Good one-way deal

$309 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
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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. 5% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 October 9, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Fri 12/58:42 pmMDW - BOS
1 stop27h 02mFrontier
Wed 12/106:00 amBOS - MDW
1 stop16h 32mFrontier
Deal found 10/8$124
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 12/38:00 amMDW - BOS
1 stop15h 01mFrontier
Mon 12/86:00 amBOS - MDW
1 stop18h 05mFrontier
Deal found 10/8$126
This Southwest deal was found by Cheapflights users on 10/7. 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 10/249:20 pmMDW - BOS
Nonstop2h 20mSouthwest
Tue 10/285:40 pmBOS - MDW
1 stop5h 25mSouthwest
Deal found 10/7$127
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Thu 12/47:47 pmMDW - BOS
1 stop27h 57mFrontier
Tue 12/96:00 amBOS - MDW
1 stop16h 32mFrontier
Deal found 10/8$129
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Tue 12/98:00 amMDW - BOS
1 stop15h 01mFrontier
Wed 12/106:00 amBOS - MDW
1 stop16h 32mFrontier
Deal found 10/7$131
This Southwest deal was found by Cheapflights users on 10/7. 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 10/212:30 pmMDW - BOS
2 stops7h 10mSouthwest
Thu 10/235:15 amBOS - MDW
Nonstop2h 40mSouthwest
Deal found 10/7$132
This Southwest deal was found by Cheapflights users on 10/6. 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 10/1812:45 pmMDW - BOS
Nonstop2h 15mSouthwest
Wed 10/229:10 amBOS - MDW
1 stop10h 20mSouthwest
Deal found 10/6$133
This Southwest deal was found by Cheapflights users on 10/7. 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 10/285:45 amMDW - BOS
1 stop5h 05mSouthwest
Tue 10/285:40 pmBOS - MDW
1 stop5h 25mSouthwest
Deal found 10/7$137
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Thu 12/47:47 pmMDW - BOS
1 stop27h 57mFrontier
Mon 12/86:00 amBOS - MDW
1 stop18h 05mFrontier
Deal found 10/8$139
This Southwest deal was found by Cheapflights users on 10/8. 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 10/318:00 amMDW - BOS
1 stop6h 55mSouthwest
Tue 11/49:05 amBOS - MDW
2 stops10h 20mSouthwest
Deal found 10/8$142
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Fri 12/52:15 pmMDW - PWM
1 stop19h 21mMultiple Airlines
Mon 12/811:21 amPWM - MDW
2 stops12h 44mMultiple Airlines
Deal found 10/8$279
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Fri 10/245:28 pmMDW - MHT
1 stop24h 28mMultiple Airlines
Fri 10/319:59 amMHT - MDW
2 stops25h 27mMultiple Airlines
Deal found 10/7$315

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 October 9, 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

Mon 10/27

9:20 pm-12:40 am

Nonstop2h 20m

Boston Logan Intl

Thu 10/30

5:00 am-9:05 am

1 stop5h 05m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 11/8

12:50 pm-4:05 pm

Nonstop2h 15m

Boston Logan Intl

Mon 11/10

5:15 am-7:00 am

Nonstop2h 45m

$177

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 11/17

1:30 pm-4:45 pm

Nonstop2h 15m

Boston Logan Intl

Fri 11/21

5:15 am-7:00 am

Nonstop2h 45m

$177

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 11/11

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Sun 11/16

5:15 am-7:00 am

Nonstop2h 45m

$177

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 11/6

2:25 pm-5:40 pm

Nonstop2h 15m

Boston Logan Intl

Mon 11/10

5:15 am-7:00 am

Nonstop2h 45m

$177

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 11/22

8:40 pm-11:55 pm

Nonstop2h 15m

Boston Logan Intl

Sun 11/23

5:15 am-7:00 am

Nonstop2h 45m

$177

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 11/13

6:20 am-1:05 pm

1 stop5h 45m

Boston Logan Intl

Mon 11/17

5:30 am-7:15 am

Nonstop2h 45m

$187

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 11/18

6:40 am-12:55 pm

1 stop5h 15m

Boston Logan Intl

Fri 11/21

5:15 am-7:00 am

Nonstop2h 45m

$187

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 12/8

6:40 am-12:55 pm

1 stop5h 15m

Boston Logan Intl

Thu 12/11

5:30 am-7:15 am

Nonstop2h 45m

$187

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 11/5

9:35 am-4:03 pm

1 stop5h 28m

Portland

Wed 11/12

6:00 am-11:52 am

1 stop6h 52m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/8

Showing 1-10 of 48 results
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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 October 9, 2025.

One of the essential ways to save on airfare from Chicago Midway Airport to New Hampshire is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 26% on airfare.

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 October 9, 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
4,236 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 2h 20m. Southwest provides one of the quickest options available for as low as $127. The distance from Chicago Midway Airport to New Hampshire 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 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 $445 for a flight from Chicago Midway Airport to New Hampshire. The cheapest flight overall is $148 while the most popular route, (Chicago Midway - Boston Logan Intl) is currently priced at $117.

  • 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.

See more FAQs

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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 October 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$181Average$425FlexibilityNo cancel feeOn-time63%

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