$84 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 6/16. 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$167
Portland
Portlandnonstop$279
Boston
Bostonnonstop$167
Portland
Portlandnonstop$279

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

Tue, Jun 16 - Tue, Jun 23
Southwest Logo
6:05 pm - 9:20 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
$167Southwest
Mon, Jun 29 - Tue, Jun 30
Southwest Logo
7:35 pm - 10:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
$172Southwest
Sat, Jul 11 - Mon, Jul 13
Southwest Logo
5:25 am - 8:40 am
MDW
-
BOS
2h 15mnonstop
Southwest Logo
6:45 pm - 8:35 pm
BOS
-
MDW
2h 50mnonstop
$177Southwest
Thu, May 28 - Mon, Jun 1
Frontier Logo
12:27 pm - 1:24 am
MDW
-
BOS
11h 57m
1 stop
Frontier Logo
6:00 am - 11:09 am
BOS
-
MDW
6h 09m
1 stop
$180Frontier
Wed, May 13 - Wed, May 20
Frontier Logo
12:04 pm - 1:24 am
MDW
-
BOS
12h 20m
1 stop
Frontier Logo
12:01 pm - 10:02 pm
BOS
-
MDW
11h 01m
1 stop
$181Frontier
Tue, Jun 2 - Sat, Jun 6
Southwest Logo
6:00 pm - 9:20 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
5:20 am - 6:55 am
BOS
-
MDW
2h 35mnonstop
$182Southwest
Wed, May 20 - Tue, May 26
Frontier Logo
12:04 pm - 1:24 am
MDW
-
BOS
12h 20m
1 stop
Frontier Logo
6:00 am - 11:12 am
BOS
-
MDW
6h 12m
1 stop
$186Frontier
Tue, Jun 9 - Tue, Jun 16
Delta Logo
9:17 am - 3:55 pm
MDW
-
PWM
5h 38m
1 stop
Delta Logo
12:40 pm - 6:31 pm
PWM
-
MDW
6h 51m
1 stop
$289Delta
Fri, May 29 - Mon, Jun 1
Delta Logo
1:22 pm - 11:09 pm
MDW
-
PWM
8h 47m
2 stops
Delta Logo
12:50 pm - 6:33 pm
PWM
-
MDW
6h 43m
1 stop
$294Delta
Tue, Jun 9 - Tue, Jun 16
Delta Logo
12:45 pm - 11:29 pm
MDW
-
PWM
9h 44m
2 stops
Delta Logo
6:25 am - 4:16 pm
PWM
-
MDW
10h 51m
2 stops
$300Delta
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 $519 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 $519.

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 $219 on average. Morning departures are around 12% 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 $247.

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’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, 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 2 weeks before departure, which saves you about 41% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$84
Best time to beat the crowds but there is an average 41% increase in price.
Most popular time to fly with an average 2% 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.

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.
7.9
SouthwestOverall score based on 4307 reviews
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

2.0 MediocreAnonymous, May 2026
SEA - SMF
Read more Southwest reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)