$50 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 1/14. 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
0 bags

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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
In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

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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$99
Portland
Portland1 stop$128

Good to know

High season

October

Cheapest flight

$50
Most popular time to fly with an average 6% 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 January.
  • Morning departure is around 5% cheaper 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 4854 reviews
7.2Food
8.1Comfort
8.7Crew
8.2Boarding
7.7Entertainment
Airline reviews

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

10.0 ExcellentRoxann, Dec 2024MCO - STL
Read more Southwest reviews

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

Much better than the.last. flight on SW on Thanksgiving day

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

It went well. Plane wasn't full. Will be great when assigned seating is in place

Everything was great except the food. The pretzels are really crappy.

For the first time in a long time we had a flawless experience with Southwest. Both flights were early and no mechanical errors at all. We were shocked and pleasantly surprised 😮.

It was fine. For some reason the flight was much longer than usual. It may have been explained, but I had noise cancelling earbuds on and missed a couple of announcements. The crew was fine, but there was a flight attendant who kept telling dumb jokes, occasionally one I found distasteful. This was my second time with him, but luckily it was a late flight so he didn't do as many. But I heard all of today's jokes twice, which was two times too many. Good takeout and landing.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

First, my flight was a usual flight nothing exceptional or unexpected. Over all it was a normal, good flight! Second, your questionaire is wholly lacking in the proper options to which one can answer a question. Often on short flights, there is no food let alone entertainment so why isn't that reflected in your questionaire? A simple "not applicable" would cover that issue appropriately but no, your form arbitrarily enters an answer based on the initial assessment which normally isn't factual. Until you provide an accurate means of assessing flights, I'll no longer be completing of these unimpressive and misleading assessements. Thank you!

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.
1/14Tue
1 stopFrontier
6h 06mMDW-BOS
1/15Wed
1 stopFrontier
12h 57mBOS-MDW
$99
1/14Tue
1 stopFrontier
6h 06mMDW-BOS
1/15Wed
1 stopFrontier
12h 57mBOS-MDW
$100
1/14Tue
1 stopFrontier
6h 06mMDW-BOS
1/15Wed
1 stopFrontier
12h 57mBOS-MDW
$101
1/21Tue
1 stopFrontier
6h 08mMDW-BOS
1/27Mon
1 stopFrontier
10h 43mBOS-MDW
$107
1/9Thu
nonstopSouthwest
2h 15mMDW-BOS
1/13Mon
nonstopSouthwest
2h 55mBOS-MDW
$158
1/3Fri
nonstopSouthwest
2h 10mMDW-BOS
1/7Tue
nonstopSouthwest
2h 50mBOS-MDW
$179
1/9Thu
1 stop
11h 54mMDW-BOS
1/13Mon
1 stop
25h 24mBOS-MDW
$193
1/31Fri
1 stopDelta
5h 32mMDW-PWM
2/7Fri
2 stopsDelta
12h 43mPWM-MDW
$233
2/27Thu
2 stopsDelta
8h 02mMDW-PWM
3/4Tue
2 stopsDelta
8h 05mPWM-MDW
$238
12/31Tue
1 stop
27h 07mMDW-BOS
1/5Sun
2 stops
28h 50mBOS-MDW
$310

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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.
1/14Tue
1 stopFrontier
6h 06mMDW-BOS
$50
1/7Tue
1 stopFrontier
6h 06mMDW-BOS
$51
1/7Tue
1 stopFrontier
6h 06mMDW-BOS
$52
2/15Sat
1 stopFrontier
7h 11mMDW-BOS
$53
1/7Tue
nonstopSouthwest
2h 15mMDW-BOS
$79
2/28Fri
nonstopSouthwest
2h 15mMDW-BOS
$89
1/14Tue
1 stopDelta
5h 44mMDW-PWM
$114
2/15Sat
1 stopDelta
7h 14mMDW-PWM
$118
1/30Thu
3 stops
30h 38mMDW-BOS
$207
1/26Sun
3 stops
30h 38mMDW-BOS
$210

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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.
12/20Fri
nonstopSouthwest
2h 15mMDW-BOS
1/19Sun
nonstopSouthwest
2h 55mBOS-MDW
$273
12/20Fri
multi-stopFrontier
9h 00mMDW-BOS
1/6Mon
multi-stopFrontier
8h 24mBOS-MDW
$274
12/20Fri
multi-stopSouthwest
5h 10mMDW-BOS
1/19Sun
nonstopSouthwest
2h 55mBOS-MDW
$282
12/20Fri
nonstopSouthwest
2h 15mMDW-BOS
1/2Thu
nonstopSouthwest
2h 50mBOS-MDW
$294
12/22Sun
multi-stopSouthwest
4h 20mMDW-BOS
1/4Sat
nonstopSouthwest
2h 50mBOS-MDW
$298
12/20Fri
multi-stopSouthwest
5h 10mMDW-BOS
1/2Thu
nonstopSouthwest
2h 50mBOS-MDW
$303
12/19Thu
multi-stopDelta
6h 18mMDW-BOS
12/29Sun
multi-stopDelta
4h 25mBOS-MDW
$341
12/19Thu
multi-stopDelta
6h 17mMDW-BOS
12/25Wed
multi-stopDelta
4h 25mBOS-MDW
$342
12/18Wed
multi-stopFrontier
27h 35mMDW-BOS
12/28Sat
multi-stopFrontier
10h 26mBOS-MDW
$346
12/19Thu
multi-stopDelta
4h 26mMDW-BOS
12/28Sat
multi-stopDelta
4h 25mBOS-MDW
$431

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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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