$65 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 11/5. 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

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$124
Portland
Portland1 stop$307
Boston
Boston1 stop$124
Portland
Portland1 stop$307

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, Nov 12 - Sat, Nov 15
Frontier Logo
2:06 pm - 9:00 amMDW-BOS
17h 54m1 stop
Frontier Logo
11:43 am - 6:39 pmBOS-MDW
7h 56m1 stop
$124Frontier
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Thu, Nov 6 - Sun, Nov 9
Southwest Logo
9:35 am - 3:45 pmMDW-BOS
5h 10m1 stop
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
$127Southwest
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Thu, Dec 4 - Sun, Dec 7
Frontier Logo
7:47 pm - 10:22 amMDW-BOS
13h 35m1 stop
Frontier Logo
11:28 am - 6:04 pmBOS-MDW
7h 36m1 stop
$128Frontier
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Mon, Oct 27 - Sat, Nov 1
Southwest Logo
5:50 pm - 9:05 pmMDW-BOS
2h 15mnonstop
Southwest Logo
6:30 am - 4:25 pmBOS-MDW
10h 55m2 stops
$132Southwest
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Thu, Nov 6 - Mon, Nov 10
Southwest Logo
9:10 am - 6:10 pmMDW-BOS
8h 00m1 stop
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
$133Southwest
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Fri, Nov 7 - Mon, Nov 10
Southwest Logo
2:55 pm - 11:15 pmMDW-BOS
7h 20m1 stop
Southwest Logo
5:35 am - 11:10 amBOS-MDW
6h 35m1 stop
$137Southwest
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Tue, Nov 4 - Sat, Nov 8
Multiple Airlines Logo
1:56 pm - 11:59 pmMDW-BOS
33h 03m2 stops
Multiple Airlines Logo
11:43 am - 6:39 pmBOS-MDW
7h 56m1 stop
$141Multiple Airlines
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Thu, Nov 6 - Sun, Nov 9
Southwest Logo
5:15 pm - 10:55 pmMDW-BOS
4h 40m1 stop
Southwest Logo
6:50 am - 3:40 pmBOS-MDW
9h 50m1 stop
$142Southwest
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Tue, Nov 11 - Tue, Nov 18
Delta Logo
9:34 am - 4:07 pmMDW-PWM
5h 33m1 stop
Delta Logo
6:00 am - 11:52 amPWM-MDW
6h 52m1 stop
$319Delta
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Tue, Nov 11 - Tue, Nov 18
Delta Logo
12:47 pm - 11:19 pmMDW-PWM
9h 32m2 stops
Delta Logo
6:00 am - 11:52 amPWM-MDW
6h 52m1 stop
$324Delta
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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 $245 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 $245.

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 $395 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 January, when tickets cost $173 (return) on average. On the other hand, the most expensive months are September and February, when the average cost of round-trip tickets is $330 and $323 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 25% 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$65
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 10% 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 $223 on average. Morning departures are around 14% 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.

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 4241 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

2.0 MediocreThomas, Oct 2025SAT - STL
Read more Southwest reviews

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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