$118 Find Cheap Flights from Chicago Midway Airport to New Hampshire - Compare and Save

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Cheap Flights from Midway to New Hampshire

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Boston
Boston2 stops$220
Portland
Portland1 stop$302
Boston
Boston2 stops$220
Portland
Portland1 stop$302

Book Cheap Midway to New Hampshire Plane Tickets

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to New Hampshire

Sat, Dec 12 - Wed, Dec 16
Southwest Logo
10:05 am - 7:25 pmMDW  Chicago Midway-BOS Boston Logan Intl
8h 20m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington
Southwest Logo
11:20 am - 7:30 pmBOS  Boston Logan Intl-MDW Chicago Midway
9h 10m2 stops Baltimore/Washington Orlando
$220Southwest
Wed, Oct 21 - Sat, Oct 24
Southwest Logo
9:25 am - 3:35 pmMDW  Chicago Midway-BOS Boston Logan Intl
5h 10m1 stop Kansas City
Southwest Logo
5:15 am - 6:00 pmBOS  Boston Logan Intl-MDW Chicago Midway
13h 45m2 stops Denver Intl Cincinnati Cinci./N. Kentucky
$220Southwest
Wed, Oct 28 - Wed, Nov 4
Southwest Logo
1:35 pm - 9:20 pmMDW  Chicago Midway-BOS Boston Logan Intl
6h 45m2 stops Cleveland Hopkins Intl Baltimore/Washington
Southwest Logo
1:10 pm - 8:00 pmBOS  Boston Logan Intl-MDW Chicago Midway
7h 50m2 stops Lambert-St Louis Nashville Intl
$220Southwest
Wed, Dec 9 - Sat, Dec 12
Southwest Logo
1:15 pm - 9:50 pmMDW  Chicago Midway-BOS Boston Logan Intl
7h 35m2 stops Cincinnati Cinci./N. Kentucky Baltimore/Washington
Southwest Logo
11:35 am - 5:05 pmBOS  Boston Logan Intl-MDW Chicago Midway
6h 30m2 stops Baltimore/Washington Greater Rochester Intl
$220Southwest
Thu, Jan 14 - Mon, Jan 18
Southwest Logo
9:00 am - 12:15 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 15mnonstop
Southwest Logo
5:25 am - 11:55 amBOS  Boston Logan Intl-MDW Chicago Midway
7h 30m1 stop Lambert-St Louis
$225Southwest
Wed, Oct 21 - Sat, Oct 24
Southwest Logo
7:55 am - 4:05 pmMDW  Chicago Midway-BOS Boston Logan Intl
7h 10m2 stops Buffalo Baltimore/Washington
Southwest Logo
5:15 am - 6:00 pmBOS  Boston Logan Intl-MDW Chicago Midway
13h 45m2 stops Denver Intl Cincinnati Cinci./N. Kentucky
$225Southwest
Thu, Oct 29 - Thu, Nov 5
Southwest Logo
5:30 am - 8:55 amMDW  Chicago Midway-BOS Boston Logan Intl
2h 25mnonstop
Southwest Logo
2:30 pm - 10:00 pmBOS  Boston Logan Intl-MDW Chicago Midway
8h 30m1 stop Kansas City
$226Southwest
Thu, Nov 5 - Mon, Nov 9
Southwest Logo
6:45 pm - 10:05 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 20mnonstop
Southwest Logo
3:30 pm - 9:05 pmBOS  Boston Logan Intl-MDW Chicago Midway
6h 35m1 stop Nashville Intl
$226Southwest
Thu, Oct 29 - Sat, Oct 31
Delta Logo
6:44 pm - 11:59 pmMDW  Chicago Midway-BOS Boston Logan Intl
4h 15m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:15 am - 12:47 pmBOS  Boston Logan Intl-MDW Chicago Midway
4h 32m1 stop Detroit Metropolitan Wayne County
$235Delta
Thu, Nov 5 - Mon, Nov 9
Delta Logo
6:44 pm - 11:59 pmMDW  Chicago Midway-BOS Boston Logan Intl
4h 15m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:40 pm - 10:54 pmBOS  Boston Logan Intl-MDW Chicago Midway
6h 14m1 stop Atlanta Hartsfield-Jackson
$235Delta
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?

The cheapest ticket to New Hampshire from Chicago Midway Airport found in the last 5 days was to Manchester, at $257 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 $257.

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 afternoon, when round-trip flights cost $259 on average. Morning departures are around 12% 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 $296.

Can I save money by flying with a layover from Chicago Midway Airport to New Hampshire?

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?

If you are looking for a flight deal from Chicago Midway Airport to New Hampshire, look for departures on Fridays and avoid leaving on a Monday, 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 get a below average price on the flight from Chicago Midway Airport to New Hampshire, you should book around 5 weeks before departure, which saves you about 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Find deals

Good to know

Low season

January

Cheapest flight

$118
Best time to beat the crowds but there is an average 29% 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 $158 one-way - $275 round-trip

Reviews of the top airline flying from Midway to New Hampshire

 
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 4188 reviews
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
8.0Comfort
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

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.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Really full flight, checked in ASAP and still mid Cs.

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