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New Hampshire

$67+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MHT
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:01 pm
MDW
-
BOS
1 stop7h 12m
Frontier
Mon 2/96:00 am
BOS
-
MDW
1 stop6h 45m
Frontier
Deal found 1/26$133
This Southwest deal was found by Cheapflights users on 1/27. 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.
Fri 1/305:35 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Sun 2/15:20 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 1/27$135
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2811:45 am
MDW
-
BOS
1 stop6h 30m
Delta
Tue 3/36:55 am
BOS
-
MDW
1 stop6h 04m
Delta
Deal found 1/28$139
This Southwest deal was found by Cheapflights users on 1/28. 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 2/255:35 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Sun 3/15:00 am
BOS
-
MDW
Nonstop2h 55m
Southwest
Deal found 1/28$143
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
MDW
-
BOS
1 stop18h 13m
Frontier
Wed 3/46:00 am
BOS
-
MDW
1 stop14h 07m
Frontier
Deal found 1/27$145
This Southwest deal was found by Cheapflights users on 1/29. 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 1/3110:15 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Mon 2/25:30 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 1/29$146
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:15 am
MDW
-
BOS
1 stop16h 44m
Multiple Airlines
Wed 3/45:50 pm
BOS
-
MDW
1 stop21h 06m
Multiple Airlines
Deal found 1/28$147
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/116:15 am
MDW
-
BOS
2 stops16h 42m
Multiple Airlines
Wed 2/185:50 pm
BOS
-
MDW
1 stop21h 06m
Multiple Airlines
Deal found 1/27$148
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:10 am
MDW
-
BOS
1 stop18h 03m
Frontier
Tue 3/36:00 am
BOS
-
MDW
1 stop14h 07m
Frontier
Deal found 1/27$149
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/249:34 am
MDW
-
BOS
1 stop5h 19m
Delta
Sat 2/285:50 am
BOS
-
MDW
1 stop6h 13m
Delta
Deal found 1/28$152
This Southwest deal was found by Cheapflights users on 1/29. 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 2/269:20 pm
MDW
-
BOS
1 stop10h 00m
Southwest
Thu 3/56:25 pm
BOS
-
MDW
Nonstop3h 00m
Southwest
Deal found 1/29$154
This Southwest deal was found by Cheapflights users on 1/28. 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.
Sat 2/710:15 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Mon 2/95:20 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 1/28$155

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$135
(Southwest)

One-way from

$67
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$207
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. 6% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 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

Midway

Fly to

New Hampshire

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 2/28

11:45 am-7:15 pm

1 stop6h 30m

Boston Logan Intl

Sat 3/7

5:29 am-8:54 am

1 stop4h 25m

$139

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 2/25

10:49 am-5:32 pm

1 stop5h 43m

Boston Logan Intl

Sat 2/28

5:29 am-8:54 am

1 stop4h 25m

$152

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 2/25

5:35 pm-8:50 pm

Nonstop2h 15m

Boston Logan Intl

Wed 3/4

5:30 am-7:20 am

Nonstop2h 50m

$155

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 4/29

12:45 pm-4:05 pm

Nonstop2h 20m

Boston Logan Intl

Fri 5/1

6:55 pm-8:45 pm

Nonstop2h 50m

$156

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 2/9

12:30 pm-10:10 pm

1 stop8h 40m

Boston Logan Intl

Wed 2/18

5:30 am-7:20 am

Nonstop2h 50m

$162

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 4/29

12:45 pm-4:05 pm

Nonstop2h 20m

Boston Logan Intl

Thu 4/30

6:55 pm-8:45 pm

Nonstop2h 50m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 2/27

6:05 am-9:25 am

Nonstop2h 20m

Boston Logan Intl

Sun 3/1

5:00 am-6:55 am

Nonstop2h 55m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 2/25

5:35 pm-8:50 pm

Nonstop2h 15m

Boston Logan Intl

Sat 2/28

5:00 am-1:30 pm

2 stops9h 30m

$172

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 4/21

12:50 pm-7:30 pm

2 stops5h 40m

Boston Logan Intl

Sun 4/26

6:10 am-7:55 am

Nonstop2h 45m

$178

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 2/11

5:35 pm-8:50 pm

Nonstop2h 15m

Boston Logan Intl

Thu 2/12

5:35 am-11:30 am

1 stop6h 55m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 53 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 January 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 at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 20% 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 January 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
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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. Delta provides one of the quickest options available for as low as $155. 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.

  • 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 Denver 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$181Average$368FlexibilityNo cancel feeOn-time63%

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