$64 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 1/17. 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
1 adult, Economy, 0 bags

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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Flight Deals

Cheap Flights from Midway to New Hampshire

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Bostonnonstop$131
Portland
Portland1 stop$211
Boston
Bostonnonstop$131
Portland
Portland1 stop$211

Book Cheap Midway to New Hampshire Plane Tickets

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to New Hampshire

Wed, Jan 21 - Wed, Jan 28
Southwest Logo
5:35 pm - 8:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
9:35 am - 2:55 pm
BOS
-
MDW
6h 20m1 stop
$131Southwest
Sun, Jan 25 - Mon, Jan 26
Southwest Logo
6:35 pm - 9:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
$132Southwest
Sat, Jan 24 - Sun, Jan 25
Southwest Logo
5:40 pm - 8:55 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:50 am - 12:05 pm
BOS
-
MDW
7h 15m1 stop
$137Southwest
Fri, Jan 23 - Sat, Jan 24
Southwest Logo
5:35 pm - 8:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
12:55 pm - 4:55 pm
BOS
-
MDW
5h 00m1 stop
$141Southwest
Thu, Jan 15 - Sun, Jan 25
Southwest Logo
6:35 pm - 9:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:20 am - 7:10 am
BOS
-
MDW
2h 50mnonstop
$142Southwest
Thu, Feb 5 - Tue, Feb 10
Southwest Logo
9:40 am - 12:55 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
2:40 pm - 4:30 pm
BOS
-
MDW
2h 50mnonstop
$143Southwest
Tue, Jan 20 - Tue, Feb 3
Frontier Logo
1:20 pm - 1:03 am
MDW
-
BOS
10h 43m1 stop
Frontier Logo
6:00 am - 12:05 pm
BOS
-
MDW
7h 05m1 stop
$144Frontier
Tue, May 5 - Sat, May 9
Delta Logo
9:27 am - 3:58 pm
MDW
-
PWM
5h 31m1 stop
Delta Logo
12:50 pm - 6:31 pm
PWM
-
MDW
6h 41m1 stop
$229Delta
Thu, Jan 29 - Tue, Feb 3
Delta Logo
9:33 am - 10:27 pm
MDW
-
PWM
11h 54m2 stops
Delta Logo
12:10 pm - 5:55 pm
PWM
-
MDW
6h 45m1 stop
$234Delta
Thu, Feb 19 - Mon, Feb 23
Delta Logo
6:00 am - 5:14 pm
MDW
-
PWM
10h 14m2 stops
Delta Logo
2:35 pm - 10:31 pm
PWM
-
MDW
8h 56m2 stops
$240Delta
Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to New Hampshire from Chicago Midway Airport found in the last 72 hours was to Manchester, at $312 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 $312.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $312 on average.

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 March, when tickets cost $251 (return) on average. On the other hand, the most expensive months are June and May, when the average cost of round-trip tickets is $309 and $301 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 Tuesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from New Hampshire, Wednesday 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 3 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$64
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 9% 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.

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

    The cheapest time of day to fly to New Hampshire is generally in the evening, when round-trip flights cost $220 on average. Morning departures are around 18% more expensive than evening flights, on average. The most expensive time of day to fly to New Hampshire is generally in the morning, which is peak travel time and where the average cost of a ticket is $260.

Reviews of the 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 4248 reviews
7.5Entertainment
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
Airline reviews

The flight crew was extremely rude and especially not helpful when our flight was delayed.

2.0 MediocreMatthew, Jan 2026
DAL - SAN
Read more Southwest reviews

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)