$74 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 4/22. 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
Boston1 stop$140
Portland
Portlandnonstop$269
Boston
Boston1 stop$140
Portland
Portlandnonstop$269

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, Apr 29 - Tue, May 5
Frontier Logo
2:15 pm - 1:31 am
MDW
-
BOS
10h 16m
1 stop
Frontier Logo
6:00 am - 11:09 am
BOS
-
MDW
6h 09m
1 stop
$140Frontier
Tue, Apr 21 - Tue, Apr 28
Frontier Logo
2:15 pm - 1:31 am
MDW
-
BOS
10h 16m
1 stop
Frontier Logo
12:52 pm - 7:31 pm
BOS
-
MDW
7h 39m
1 stop
$145Frontier
Tue, May 12 - Tue, May 12
Southwest Logo
12:45 pm - 4:05 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
6:00 pm - 10:15 pm
BOS
-
MDW
5h 15m
1 stop
$149Southwest
Mon, Apr 20 - Wed, Apr 29
Frontier Logo
2:15 pm - 11:45 am
MDW
-
BOS
20h 30m
1 stop
Frontier Logo
6:00 am - 10:14 pm
BOS
-
MDW
17h 14m
1 stop
$151Frontier
Tue, May 5 - Sat, May 9
Southwest Logo
6:00 pm - 9:20 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
3:30 pm - 5:15 pm
BOS
-
MDW
2h 45mnonstop
$153Southwest
Tue, May 12 - Tue, May 19
Southwest Logo
2:35 pm - 10:40 pm
MDW
-
BOS
7h 05m
2 stops
Southwest Logo
10:45 am - 12:25 pm
BOS
-
MDW
2h 40mnonstop
$154Southwest
Tue, Apr 21 - Tue, Apr 28
Frontier Logo
2:15 pm - 1:31 am
MDW
-
BOS
10h 16m
1 stop
Frontier Logo
12:52 pm - 7:31 pm
BOS
-
MDW
7h 39m
1 stop
$156Frontier
Wed, Apr 29 - Sun, May 3
Southwest Logo
12:45 pm - 4:05 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
10:35 am - 12:15 pm
BOS
-
MDW
2h 40mnonstop
$158Southwest
Wed, May 6 - Wed, May 6
Southwest Logo
5:30 am - 1:40 pm
MDW
-
BOS
7h 10m
1 stop
Southwest Logo
5:55 pm - 9:50 pm
BOS
-
MDW
4h 55m
1 stop
$159Southwest
Tue, Jun 9 - Tue, Jun 16
Delta Logo
1:16 pm - 11:29 pm
MDW
-
PWM
9h 13m
2 stops
Delta Logo
6:00 am - 4:16 pm
PWM
-
MDW
11h 16m
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 $217 on average. Morning departures are around 15% 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 $249.

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 July, when tickets cost $247 (return) on average. On the other hand, the most expensive months are January and April, when the average cost of round-trip tickets is $414 and $325 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 2 weeks before departure, which saves you about 42% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$74
Best time to beat the crowds but there is an average 39% increase in price.
Most popular time to fly with an average 1% 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.

Top tips for finding cheap flights to New Hampshire

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Boston $102 one-way - $197 round-trip

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 4334 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

One of the best airlines for fast boarding, on time arrivals, and top notch service!

10.0 ExcellentSunderesh, Apr 2026
OKC - AUS
Read more Southwest reviews

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

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

Information on your arrival and departure airports