$59 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 12/25. 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$124
Portland
Portland1 stop$229
Boston
Bostonnonstop$124
Portland
Portland1 stop$229

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

Fri, Dec 26 - Thu, Jan 1
Southwest Logo
5:30 am - 8:45 amMDW-BOS
2h 15mnonstop
Southwest Logo
5:30 am - 7:15 amBOS-MDW
2h 45mnonstop
$124Southwest
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Sat, Dec 13 - Sat, Dec 13
Southwest Logo
9:50 am - 1:10 pmMDW-BOS
2h 20mnonstop
Southwest Logo
4:45 pm - 6:30 pmBOS-MDW
2h 45mnonstop
$127Southwest
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Sat, Jan 17 - Sun, Jan 18
Southwest Logo
10:15 am - 1:30 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:30 am - 7:20 amBOS-MDW
2h 50mnonstop
$132Southwest
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Fri, Dec 12 - Sun, Dec 14
Southwest Logo
7:15 pm - 10:30 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
$137Southwest
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Wed, Feb 4 - Sun, Feb 8
Frontier Logo
1:20 pm - 1:03 amMDW-BOS
10h 43m1 stop
Frontier Logo
6:00 am - 11:45 amBOS-MDW
6h 45m1 stop
$146Frontier
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Sat, Dec 13 - Wed, Dec 17
Multiple Airlines Logo
6:00 am - 11:56 pmMDW-BOS
16h 56m2 stops
Multiple Airlines Logo
8:11 pm - 9:58 pmBOS-MDW
26h 47m1 stop
$147Multiple Airlines
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Thu, Jan 29 - Mon, Feb 2
Frontier Logo
5:01 pm - 1:13 amMDW-BOS
7h 12m1 stop
Frontier Logo
6:00 am - 11:45 amBOS-MDW
6h 45m1 stop
$149Frontier
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Sat, Dec 13 - Wed, Dec 17
Multiple Airlines Logo
6:00 am - 10:22 amMDW-BOS
27h 22m1 stop
Multiple Airlines Logo
8:11 pm - 9:58 pmBOS-MDW
26h 47m1 stop
$151Multiple Airlines
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Sun, Jan 4 - Sat, Jan 10
Delta Logo
9:29 am - 4:08 pmMDW-PWM
5h 39m1 stop
Delta Logo
5:30 am - 10:32 amPWM-MDW
6h 02m1 stop
$229Delta
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Sun, Jan 4 - Sat, Jan 10
Delta Logo
9:29 am - 4:08 pmMDW-PWM
5h 39m1 stop
Delta Logo
6:00 am - 4:29 pmPWM-MDW
11h 29m2 stops
$234Delta
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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 $327 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 $327.

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 $457, 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 $198 (return) on average. On the other hand, the most expensive months are September and November, when the average cost of round-trip tickets is $330 and $318 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 Wednesdays 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 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

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Good to know

Low seasonJanuary
Cheapest flight$59
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 11% lower on average.
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 $222 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 afternoon, which is peak travel time and where the average cost of a ticket is $273.

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 $65 one-way - $172 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 4251 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
Airline reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

10.0 ExcellentDavid, Nov 2025BUF - PHX
Read more Southwest reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)