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New Hampshire

$79+ 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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MHT
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
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 March 17, 2026.

This Southwest deal was found by Cheapflights users on 3/13. 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 4/99:25 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Mon 4/133:45 pm
BOS
-
MDW
Nonstop2h 45m
Southwest
Deal found 3/13$157
This Southwest deal was found by Cheapflights users on 3/13. 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 4/97:40 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Sun 4/126:10 am
BOS
-
MDW
Nonstop2h 45m
Southwest
Deal found 3/13$167
This Southwest deal was found by Cheapflights users on 3/13. 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 3/312:35 pm
MDW
-
BOS
Nonstop2h 10m
Southwest
Wed 4/86:20 pm
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 3/13$171
This Southwest deal was found by Cheapflights users on 3/13. 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 5/127:50 am
MDW
-
BOS
2 stops7h 05m
Southwest
Tue 5/192:25 pm
BOS
-
MDW
Nonstop2h 40m
Southwest
Deal found 3/13$172
This Southwest deal was found by Cheapflights users on 3/14. 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.
Thu 5/282:10 pm
MDW
-
BOS
1 stop8h 00m
Southwest
Tue 6/22:25 pm
BOS
-
MDW
Nonstop2h 40m
Southwest
Deal found 3/14$173
This Southwest deal was found by Cheapflights users on 3/13. 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 4/2110:10 am
MDW
-
BOS
2 stops11h 20m
Southwest
Thu 4/233:45 pm
BOS
-
MDW
Nonstop2h 45m
Southwest
Deal found 3/13$178
This Frontier deal was found by Cheapflights users on 3/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/222:15 pm
MDW
-
BOS
1 stop10h 16m
Frontier
Tue 4/2812:52 pm
BOS
-
MDW
1 stop7h 39m
Frontier
Deal found 3/12$180
This Southwest deal was found by Cheapflights users on 3/13. 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 5/282:10 pm
MDW
-
BOS
2 stops8h 45m
Southwest
Mon 6/16:45 pm
BOS
-
MDW
1 stop5h 00m
Southwest
Deal found 3/13$182
This Southwest deal was found by Cheapflights users on 3/12. 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 3/172:35 pm
MDW
-
BOS
Nonstop2h 10m
Southwest
Thu 3/1911:50 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 3/12$185
This Southwest deal was found by Cheapflights users on 3/12. 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 6/46:55 pm
MDW
-
PWM
Nonstop2h 15m
Southwest
Sun 6/76:45 am
PWM
-
MDW
Nonstop2h 35m
Southwest
Deal found 3/12$249
This Southwest deal was found by Cheapflights users on 3/16. 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 5/282:10 pm
MDW
-
PWM
2 stops8h 15m
Southwest
Thu 6/47:40 am
PWM
-
MDW
Nonstop2h 35m
Southwest
Deal found 3/16$264
This Southwest deal was found by Cheapflights users on 3/15. 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 5/89:00 am
MDW
-
PWM
1 stop6h 15m
Southwest
Sun 5/104:20 pm
PWM
-
MDW
1 stop6h 15m
Southwest
Deal found 3/15$269

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 March 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

April

Cheapest in

January

Average price

$225

Good round-trip deal

$475 or less

Good one-way deal

$224 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. 4% potential increase in price ($11 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 March 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 March 17, 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

Thu 4/30

7:40 am-10:55 am

Nonstop2h 15m

Boston Logan Intl

Mon 5/4

10:40 am-12:20 pm

Nonstop2h 40m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 4/21

7:45 am-11:00 am

Nonstop2h 15m

Boston Logan Intl

Tue 4/28

12:55 pm-8:00 pm

1 stop8h 05m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 6/10

10:10 am-5:45 pm

2 stops6h 35m

Boston Logan Intl

Sat 6/13

5:20 am-6:55 am

Nonstop2h 35m

$202

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 4/7

6:00 pm-9:20 pm

Nonstop2h 20m

Boston Logan Intl

Fri 4/10

3:45 pm-5:30 pm

Nonstop2h 45m

$217

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 4/2

3:30 pm-6:45 pm

Nonstop2h 15m

Boston Logan Intl

Fri 4/3

3:10 pm-4:55 pm

Nonstop2h 45m

$247

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 6/4

6:55 pm-10:10 pm

Nonstop2h 15m

Portland

Sun 6/7

6:45 am-8:20 am

Nonstop2h 35m

$249

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 4/9

2:10 pm-11:55 pm

2 stops8h 45m

Boston Logan Intl

Sun 4/12

6:10 am-7:55 am

Nonstop2h 45m

$257

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 4/30

2:10 pm-11:55 pm

2 stops8h 45m

Boston Logan Intl

Thu 5/7

5:50 pm-11:55 pm

1 stop7h 05m

$257

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 5/28

2:10 pm-11:25 pm

2 stops8h 15m

Portland

Thu 6/4

7:40 am-9:15 am

Nonstop2h 35m

$264

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 5/3

4:05 pm-12:05 am

2 stops7h 00m

Boston Logan Intl

Tue 5/5

8:10 am-3:45 pm

2 stops8h 35m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/12

Showing 1-10 of 50 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 March 17, 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 morning could potentially save you up to 22% 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 March 14, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to New Hampshire flight should consider departing on Friday evenings when fares are most often at their lowest. Friday afternoons 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 March 17, 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
4,320 reviews

Entertainment

7.5

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..
Southwest
8.0
Very good
4,320 reviews
Southwest
8.0
Very good
4,320 reviews

Entertainment

7.5

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..

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 $157. 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 $372 for a flight from Chicago Midway Airport to New Hampshire. The cheapest flight overall is $158 while the most popular route, (Chicago Midway - Boston Logan Intl) is currently priced at $157.

  • 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 March 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$181Average$368FlexibilityNo cancel feeOn-time63%

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