$96 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 7/18. 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$179
Portland
Portland2 stops$293
Boston
Bostonnonstop$179
Portland
Portland2 stops$293

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, Jul 10 - Wed, Jul 15
Southwest Logo
7:35 pm - 10:55 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
$179Southwest
Tue, Jul 7 - Tue, Jul 14
Southwest Logo
2:40 pm - 6:00 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
$180Southwest
Mon, Jun 29 - Sat, Jul 4
Southwest Logo
9:20 am - 12:40 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
5:40 pm - 7:30 pm
BOS
-
MDW
2h 50mnonstop
$182Southwest
Tue, Jul 7 - Sat, Jul 11
Southwest Logo
2:40 pm - 6:00 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
7:55 am - 9:30 am
BOS
-
MDW
2h 35mnonstop
$183Southwest
Sat, Jul 4 - Wed, Jul 8
Southwest Logo
12:45 pm - 8:25 pm
MDW
-
BOS
6h 40m
2 stops
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
$185Southwest
Wed, Jul 15 - Wed, Jul 22
Southwest Logo
12:45 pm - 4:05 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
7:30 am - 9:10 am
BOS
-
MDW
2h 40mnonstop
$187Southwest
Thu, Aug 13 - Wed, Aug 19
Southwest Logo
5:45 am - 9:00 am
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:50 pm - 10:20 pm
BOS
-
MDW
5h 30m
1 stop
$188Southwest
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
$189Southwest
Sat, Aug 29 - Tue, Sep 1
Delta Logo
6:05 am - 2:17 pm
MDW
-
PWM
7h 12m
2 stops
Delta Logo
11:50 am - 6:01 pm
PWM
-
MDW
7h 11m
1 stop
$293Delta
Sat, Aug 29 - Tue, Sep 1
Delta Logo
6:05 am - 2:17 pm
MDW
-
PWM
7h 12m
2 stops
Delta Logo
6:30 am - 3:44 pm
PWM
-
MDW
10h 14m
2 stops
$299Delta
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 5 days was to Manchester, at $329 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 5 days was $329.

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 $223 on average. Morning departures are around 17% 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 $261.

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, 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 3 weeks before departure, which saves you about 42% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$96
Best time to beat the crowds but there is an average 38% increase in price.
Most popular time to fly and prices are also 25% 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.

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 $128 one-way - $231 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.
7.9
SouthwestOverall score based on 4235 reviews
8.1Boarding
7.0Food
7.5Entertainment
8.0Comfort
8.6Crew
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)