$54 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 2/12. 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.
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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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Best New Hampshire Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Boston
Boston1 stop$101
Portland
Portland1 stop$239

Good to know

Low season

April

High season

October

Cheapest flight

$54
Best time to beat the crowds with an average 4% drop 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.

See more FAQs

Top tips for finding cheap flights to New Hampshire

  • High season is considered to be May, June and July. The cheapest month to fly from Chicago is February.
  • Morning departure is around 22% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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.
8.1
SouthwestOverall score based on 4662 reviews
7.2Food
8.1Comfort
8.7Crew
8.2Boarding
7.7Entertainment
Airline reviews

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

10.0 ExcellentRachel, Jan 2025TPA - MDW
Read more Southwest reviews

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

It was 2 hours 45 minutes late, for no apparently clear reason.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Book cheap flights from Chicago to New Hampshire

Recent round-trip flight deals

 
These are the cheapest round-trip flights from Chicago to New Hampshire found on KAYAK in the last 72 hours.
3/1Sat
1 stopFrontier
7h 11mMDW-BOS
3/10Mon
1 stopFrontier
7h 24mBOS-MDW
$101
3/1Sat
1 stopFrontier
7h 11mMDW-BOS
3/10Mon
1 stopFrontier
13h 49mBOS-MDW
$108
3/1Sat
1 stopFrontier
7h 11mMDW-BOS
3/10Mon
1 stopFrontier
13h 49mBOS-MDW
$110
3/1Sat
1 stopFrontier
7h 11mMDW-BOS
3/10Mon
1 stopFrontier
7h 24mBOS-MDW
$111
2/19Wed
nonstopSouthwest
2h 15mMDW-BOS
2/23Sun
nonstopSouthwest
2h 55mBOS-MDW
$157
2/26Wed
nonstopSouthwest
2h 15mMDW-BOS
3/3Mon
nonstopSouthwest
2h 50mBOS-MDW
$167
2/19Wed
1 stopDelta
5h 30mMDW-PWM
2/20Thu
2 stopsDelta
8h 05mPWM-MDW
$283
2/19Wed
1 stopDelta
5h 30mMDW-PWM
2/21Fri
1 stopDelta
7h 25mPWM-MDW
$310
6/19Thu
2 stops
25h 23mMDW-PWM
6/22Sun
2 stops
22h 12mPWM-MDW
$553
6/19Thu
3 stops
38h 26mMDW-PWM
6/22Sun
2 stops
22h 12mPWM-MDW
$664

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to New Hampshire found on KAYAK in the last 72 hours.
2/12Wed
1 stopFrontier
7h 11mMDW-BOS
$54
3/12Wed
1 stopFrontier
8h 17mMDW-BOS
$55
2/19Wed
nonstopSouthwest
2h 15mMDW-BOS
$79
3/5Wed
nonstopSouthwest
2h 15mMDW-BOS
$89
2/18Tue
1 stopDelta
5h 50mMDW-PWM
$109
2/18Tue
2 stopsDelta
11h 51mMDW-PWM
$114
5/23Fri
1 stopAllegiant Air
12h 08mMDW-BOS
$160
5/5Mon
3 stops
28h 20mMDW-BOS
$175
5/12Mon
3 stops
28h 20mMDW-BOS
$199
4/27Sun
2 stopsAllegiant Air
21h 28mMDW-BOS
$247

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Last minute flights from Midway to New Hampshire

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to New Hampshire that are departing in the next 10 days.
1/25Sat
nonstopSouthwest
2h 15mMDW-BOS
2/4Tue
nonstopSouthwest
2h 50mBOS-MDW
$282
1/24Fri
multi-stopFrontier
7h 50mMDW-BOS
1/27Mon
multi-stopFrontier
10h 43mBOS-MDW
$290
1/25Sat
multi-stopSouthwest
6h 50mMDW-BOS
2/4Tue
nonstopSouthwest
2h 50mBOS-MDW
$292
1/23Thu
nonstopSouthwest
2h 15mMDW-BOS
2/3Mon
nonstopSouthwest
2h 55mBOS-MDW
$302
1/25Sat
nonstopSouthwest
2h 15mMDW-BOS
1/28Tue
multi-stopSouthwest
8h 50mBOS-MDW
$307
1/23Thu
multi-stopSouthwest
7h 05mMDW-BOS
2/3Mon
nonstopSouthwest
2h 50mBOS-MDW
$312
1/23Thu
multi-stopSouthwest
5h 55mMDW-BOS
2/3Mon
nonstopSouthwest
2h 50mBOS-MDW
$317
1/24Fri
multi-stopSouthwest
7h 50mMDW-BOS
1/27Mon
nonstopSouthwest
2h 50mBOS-MDW
$322
1/24Fri
multi-stopFrontier
7h 50mMDW-BOS
1/26Sun
multi-stopFrontier
29h 28mBOS-MDW
$340
1/23Thu
multi-stopDelta
5h 11mMDW-BOS
1/24Fri
multi-stopDelta
6h 04mBOS-MDW
$677

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

Information on your arrival and departure airports

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