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New Hampshire

$109+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MHT
Aug 28 — Sep 41
Fri 8/28
Fri 9/4
1 adult, Economy
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Cheap 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 July 29, 2026.

This Southwest deal was found by Cheapflights users on 7/28. 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 9/96:00 pm
MDW
-
BOS
Nonstop2h 25m
Southwest
Wed 9/167:30 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/28$217
This Southwest deal was found by Cheapflights users on 7/29. 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 9/127:40 am
MDW
-
BOS
Nonstop2h 20m
Southwest
Mon 9/146:40 pm
BOS
-
MDW
Nonstop2h 45m
Southwest
Deal found 7/29$222
This Southwest deal was found by Cheapflights users on 7/24. 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 8/126:00 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Fri 8/146:40 pm
BOS
-
MDW
Nonstop2h 40m
Southwest
Deal found 7/24$231
This Southwest deal was found by Cheapflights users on 7/27. 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 10/12:50 pm
MDW
-
BOS
2 stops5h 30m
Southwest
Tue 10/610:55 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/27$233
This Southwest deal was found by Cheapflights users on 7/27. 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 9/88:30 am
MDW
-
MHT
Nonstop2h 20m
Southwest
Tue 9/156:15 pm
MHT
-
MDW
Nonstop2h 20m
Southwest
Deal found 7/27$235
This Southwest deal was found by Cheapflights users on 7/28. 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 8/145:45 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Tue 8/187:15 pm
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/28$236
This Southwest deal was found by Cheapflights users on 7/28. 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 8/2810:30 am
MDW
-
BOS
1 stop6h 20m
Southwest
Sun 8/309:05 pm
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/28$237
This Southwest deal was found by Cheapflights users on 7/27. 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 9/1211:25 am
MDW
-
BOS
Nonstop2h 20m
Southwest
Sun 9/135:30 am
BOS
-
MDW
1 stop5h 25m
Southwest
Deal found 7/27$241
This Southwest deal was found by Cheapflights users on 7/29. 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 8/277:55 pm
MDW
-
BOS
1 stop11h 05m
Southwest
Sun 8/307:30 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/29$243
This Delta deal was found by Cheapflights users on 7/24. 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.
Sat 8/229:24 am
MDW
-
PWM
2 stops11h 07m
Delta
Wed 8/261:12 pm
PWM
-
MDW
2 stops10h 24m
Delta
Deal found 7/24$275
This Southwest deal was found by Cheapflights users on 7/26. 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 8/256:50 pm
MDW
-
PWM
Nonstop2h 15m
Southwest
Tue 9/17:45 am
PWM
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/26$276
This Southwest deal was found by Cheapflights users on 7/25. 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 8/229:55 am
MDW
-
PWM
2 stops10h 05m
Southwest
Wed 8/267:45 am
PWM
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/25$277

Find 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 July 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(Southwest)

One-way from

$109
(Southwest)

Popular in

April

Cheapest in

January

Average price

$263

Good round-trip deal

$352 or less

Good one-way deal

$283 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
Search Deals
From Chicago Midway to New Hampshire
Search Deals
One-way flight from Chicago Midway to New Hampshire
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($3 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to New Hampshire.
Search Deals
Price to beat on a one-way flight from Chicago Midway to New Hampshire.
Search Deals

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 July 29, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to New Hampshire that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 11/11

6:25 pm-9:40 pm

Nonstop2h 15m

Boston Logan Intl

Mon 11/16

7:05 am-8:50 am

Nonstop2h 45m

$222

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 9/9

6:30 am-2:40 pm

1 stop7h 10m

Boston Logan Intl

Wed 9/16

10:05 am-11:35 am

Nonstop2h 30m

$227

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/4

8:30 am-11:55 am

Nonstop2h 25m

Boston Logan Intl

Mon 12/7

7:05 am-8:50 am

Nonstop2h 45m

$227
Quickest round-trip

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Thu 11/12

1:35 pm-4:40 pm

Nonstop2h 05m

Manchester

Tue 11/17

7:20 am-8:55 am

Nonstop2h 35m

$235

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Thu 9/3

6:10 pm-9:30 pm

Nonstop2h 20m

Manchester

Tue 9/8

6:15 pm-7:35 pm

Nonstop2h 20m

$235

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Wed 9/9

8:30 am-11:50 am

Nonstop2h 20m

Manchester

Wed 9/16

6:15 pm-7:35 pm

Nonstop2h 20m

$235

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Tue 9/8

5:55 pm-9:15 pm

Nonstop2h 20m

Manchester

Tue 9/15

6:15 pm-7:35 pm

Nonstop2h 20m

$235

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 8/17

8:15 am-11:40 am

Nonstop2h 25m

Boston Logan Intl

Fri 8/21

8:20 pm-10:00 pm

Nonstop2h 40m

$236

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 8/17

10:30 am-5:50 pm

1 stop6h 20m

Boston Logan Intl

Tue 8/18

10:05 am-11:35 am

Nonstop2h 30m

$237

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 8/21

6:30 pm-9:50 pm

Nonstop2h 20m

Boston Logan Intl

Sat 8/22

5:30 am-9:30 am

1 stop5h 00m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

Showing 1-10 of 56 resultsSorted by cheapest first
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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 July 29, 2026.

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 evening tend to be the most expensive. A flight at noon could potentially save you up to 32% on airfare.

What is the cheapest day to fly from Chicago Midway Airport to New Hampshire?

Use this chart to determine the cheapest time to fly round-trip from Midway to New Hampshire. Price data was last updated on July 25, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to New Hampshire flight should consider departing on Saturday mornings when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 July 29, 2026.
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
4,227 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,227 reviews
Southwest
8.0
Very good
4,227 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore 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 15m. Southwest provides one of the quickest options available for as low as $222. 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 $366 for a flight from Chicago Midway Airport to New Hampshire. The cheapest flight overall is $138 while the most popular route, (Chicago Midway - Boston Logan Intl) is currently priced at $217.

  • 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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Midway to Miami flights
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Midway to LaGuardia flights
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Midway to Seattle flights
Midway to Los Angeles flights
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Midway to Atlanta flights
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Midway to Fort Lauderdale flights
Midway to Orlando flights
Midway to Dulles Intl flights
O'Hare Intl to Santa Ana flights
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O'Hare Intl to Portland flights
O'Hare Intl to Jackson flights
Midway to Minneapolis flights

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 July 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$181Average$429FlexibilityNo cancel feeOn-time63%

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