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$49 Find Cheap Flights from Chicago Midway Airport to New Hampshire

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to New Hampshire departing on 4/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult

KAYAK searches hundreds of travel sites at once for deals on flights to New Hampshire

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to New Hampshire, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to New Hampshire, as well as popular online travel agencies
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Best New Hampshire Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Boston
Bostonnonstop$97
Portland
Portland1 stop$219

Cheap Flight Deals from Midway to New Hampshire (MDW-USNH)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to New Hampshire that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to New Hampshire

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to New Hampshire.
Discover the best prices for you by selecting your travel dates on KAYAK.
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Southwest Logo
12:10 pm - 3:30 pmMDW-BOS
2h 20mnonstop
Southwest Logo
5:45 am - 7:20 amBOS-MDW
2h 35mnonstop
$97Southwest
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Sat, Apr 12 - Mon, Apr 14
Southwest Logo
12:10 pm - 3:30 pmMDW-BOS
2h 20mnonstop
Southwest Logo
5:00 am - 10:35 amBOS-MDW
6h 35m1 stop
$107Southwest
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Sat, Apr 12 - Mon, Apr 14
Southwest Logo
6:35 am - 4:25 pmMDW-BOS
8h 50m1 stop
Southwest Logo
5:45 pm - 7:25 pmBOS-MDW
2h 40mnonstop
$112Southwest
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Sat, May 3 - Sat, May 10
Southwest Logo
5:50 am - 3:05 pmMDW-BOS
8h 15m1 stop
Southwest Logo
6:15 pm - 9:50 pmBOS-MDW
4h 35m1 stop
$116Southwest
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Sun, May 11 - Wed, May 21
Southwest Logo
8:30 pm - 11:45 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:30 am - 7:05 amBOS-MDW
2h 35mnonstop
$117Southwest
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Thu, Jul 17 - Sun, Jul 20
Frontier Logo
1:19 pm - 1:05 amMDW-BOS
10h 46m1 stop
Frontier Logo
12:58 pm - 11:47 pmBOS-MDW
11h 49m1 stop
$198Frontier
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Thu, May 8 - Mon, May 12
Frontier Logo
4:00 pm - 9:34 amMDW-BOS
16h 34m1 stop
Frontier Logo
10:14 am - 10:40 pmBOS-MDW
13h 26m1 stop
$200Frontier
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Thu, May 1 - Sun, May 4
Delta Logo
4:24 pm - 12:28 amMDW-PWM
7h 04m1 stop
Delta Logo
11:44 am - 5:45 pmPWM-MDW
7h 01m1 stop
$233Delta
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Tue, Jul 1 - Thu, Jul 3
Delta Logo
12:48 pm - 12:14 amMDW-PWM
10h 26m2 stops
Delta Logo
1:30 pm - 9:14 pmPWM-MDW
8h 44m1 stop
$254Delta
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Sat, May 10 - Sat, May 17
Allegiant Air Logo
8:04 pm - 9:12 amMDW-BOS
12h 08m1 stop
Allegiant Air Logo
12:34 pm - 2:04 pmBOS-MDW
26h 30m1 stop
$310Allegiant Air
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Fri, May 23 - Sun, May 25

KAYAK's insights & trends for Midway to New Hampshire flights

Get data-powered insights and trends into flights from Midway to New Hampshire to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to New Hampshire flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to New Hampshire.
The cheapest ticket to New Hampshire from Chicago Midway Airport found in the last 72 hours was to Manchester, at $277 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Manchester (MHT), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $277.

What is the cheapest time of day to fly to New Hampshire?

The average price for all round-trip flights from Chicago Midway Airport to New Hampshire depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to New Hampshire is generally in the evening, when round-trip flights cost $229 on average. Morning departures are around 13% more expensive than evening flights, on average. The most expensive time of day to fly to New Hampshire is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $298.

Can I save money by flying with a layover from Chicago Midway Airport to New Hampshire?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.
No, with an average price for the route of $218, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to New Hampshire, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to New Hampshire is January, when tickets cost $185 (return) on average. On the other hand, the most expensive months are February and June, when the average cost of round-trip tickets is $323 and $322 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to New Hampshire?

The average price of all round-trip flights from Chicago Midway Airport to New Hampshire clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Chicago Midway Airport to New Hampshire, look for departures on Saturdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from New Hampshire, Thursday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Chicago Midway Airport to New Hampshire?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to New Hampshire, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.
To get a below average price on the flight from Chicago Midway Airport to New Hampshire, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.
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Good to know

Low season

July

High season

October

Cheapest flight

$49
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly with an average 5% increase in price.
Flight from Chicago Midway Airport to Boston

FAQs - booking New Hampshire flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to New Hampshire?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to New Hampshire.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to New Hampshire?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to New Hampshire is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to New Hampshire?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago Midway Airport to New Hampshire with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to New Hampshire?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago Midway Airport to New Hampshire up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Midway to New Hampshire

 
See real verified KAYAK customer reviews for airlines flying from Chicago to New Hampshire. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to New Hampshire? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4277 reviews
8.2Boarding
8.0Comfort
8.7Crew
7.1Food
7.6Entertainment
Airline reviews

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

6.0 GoodCarolynn, Mar 2025KOA - SMF
Read more Southwest reviews

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Short flight with plenty of open seats. Drinks and snacks were still provided even on such a short flight. <1 hr

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

Very good. Sad to learn Southwest is going start to charge for bags

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

WiFi on the flight was not working. Thus, entertainment options were limited.

Everything you need to know for your flight from Midway to New Hampshire

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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