$68 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 2/16. 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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Cheap Flights from Midway to New Hampshire

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Bostonnonstop$132
Portland
Portland2 stops$244
Boston
Bostonnonstop$132
Portland
Portland2 stops$244

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, Apr 3 - Sat, Apr 4
Southwest Logo
3:30 pm - 6:45 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
6:30 am - 8:20 am
BOS
-
MDW
2h 50mnonstop
$132Southwest
Sat, Mar 7 - Mon, Mar 9
Southwest Logo
7:40 am - 10:55 am
MDW
-
BOS
2h 15mnonstop
Southwest Logo
6:25 pm - 8:25 pm
BOS
-
MDW
3h 00mnonstop
$133Southwest
Thu, Feb 26 - Thu, Mar 5
Southwest Logo
6:05 am - 9:25 am
MDW
-
BOS
2h 20mnonstop
Southwest Logo
11:50 am - 1:40 pm
BOS
-
MDW
2h 50mnonstop
$137Southwest
Thu, Mar 26 - Thu, Apr 2
Southwest Logo
11:15 am - 4:55 pm
MDW
-
BOS
4h 40m
1 stop
Southwest Logo
6:25 pm - 8:25 pm
BOS
-
MDW
3h 00mnonstop
$142Southwest
Thu, Feb 26 - Fri, Feb 27
Southwest Logo
6:05 am - 9:25 am
MDW
-
BOS
2h 20mnonstop
Southwest Logo
5:00 am - 6:55 am
BOS
-
MDW
2h 55mnonstop
$146Southwest
Sun, Mar 1 - Tue, Mar 3
Southwest Logo
6:05 am - 9:25 am
MDW
-
BOS
2h 20mnonstop
Southwest Logo
5:50 am - 11:35 am
BOS
-
MDW
6h 45m
1 stop
$147Southwest
Sat, Mar 7 - Sat, Mar 14
Southwest Logo
7:40 am - 10:55 am
MDW
-
BOS
2h 15mnonstop
Southwest Logo
6:30 am - 8:20 am
BOS
-
MDW
2h 50mnonstop
$148Southwest
Tue, May 5 - Tue, May 12
Delta Logo
12:53 pm - 11:24 pm
MDW
-
PWM
9h 31m
2 stops
Delta Logo
12:52 pm - 6:14 pm
PWM
-
MDW
6h 22m
1 stop
$244Delta
Thu, Mar 12 - Mon, Mar 16
Delta Logo
9:35 am - 4:06 pm
MDW
-
PWM
5h 31m
1 stop
Delta Logo
5:23 am - 12:02 pm
PWM
-
MDW
7h 39m
1 stop
$284Delta
Sat, Feb 21 - Wed, Feb 25
Multiple Airlines Logo
6:00 am - 10:43 am
MDW
-
MHT
27h 43m
2 stops
Multiple Airlines Logo
6:09 pm - 2:26 pm
MHT
-
MDW
21h 17m
1 stop
$335Multiple Airlines
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 $304 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 $304.

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 $304, 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 July, when tickets cost $247 (return) on average. On the other hand, the most expensive months are January and February, when the average cost of round-trip tickets is $414 and $335 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 3 weeks before departure, which saves you about 43% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$68
Best time to beat the crowds but there is an average 41% increase in price.
Most popular time to fly with an average 5% 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.

  • 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 $218 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 morning, which is peak travel time and where the average cost of a ticket is $256.

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 4280 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

10.0 ExcellentAnonymous, Feb 2026
STL - DAL
Read more Southwest reviews

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

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

Information on your arrival and departure airports