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Cheap flights from New Hampshire to Chicago from $68

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New Hampshire to Chicago departing on 2/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from New Hampshire to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
3:45 pm - 5:30 pm
BOS
-
MDW
2h 45mnonstop
Southwest Logo
7:00 pm - 10:20 pm
MDW
-
BOS
2h 20mnonstop
$132Southwest
Fri, May 1 - Mon, May 4
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
7:40 am - 10:55 am
MDW
-
BOS
2h 15mnonstop
$133Southwest
Wed, Mar 4 - Sat, Mar 7
Southwest Logo
3:10 pm - 4:55 pm
BOS
-
MDW
2h 45mnonstop
Southwest Logo
3:30 pm - 6:45 pm
MDW
-
BOS
2h 15mnonstop
$137Southwest
Mon, Mar 9 - Thu, Mar 12
Southwest Logo
6:55 pm - 8:45 pm
BOS
-
MDW
2h 50mnonstop
Southwest Logo
7:40 am - 10:55 am
MDW
-
BOS
2h 15mnonstop
$142Southwest
Fri, Apr 10 - Sun, Apr 12
Multiple Airlines Logo
5:50 pm - 1:56 pm
BOS
-
MDW
21h 06m
1 stop
Multiple Airlines Logo
5:16 pm - 1:13 am
MDW
-
BOS
6h 57m
1 stop
$145Multiple Airlines
Wed, Feb 25 - Thu, Feb 26
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
5:35 pm - 8:50 pm
MDW
-
BOS
2h 15mnonstop
$146Southwest
Wed, Feb 18 - Wed, Feb 18
Frontier Logo
6:00 am - 4:16 pm
BOS
-
MDW
11h 16m
1 stop
Frontier Logo
2:19 pm - 1:13 am
MDW
-
BOS
9h 54m
1 stop
$148Frontier
Thu, Feb 26 - Mon, Mar 2
Multiple Airlines Logo
5:50 pm - 1:56 pm
BOS
-
MDW
21h 06m
1 stop
Multiple Airlines Logo
2:19 pm - 4:45 pm
MDW
-
BOS
25h 26m
2 stops
$149Multiple Airlines
Wed, Feb 25 - Mon, Mar 2
Delta Logo
5:31 am - 11:59 am
PWM
-
MDW
7h 28m
1 stop
Delta Logo
9:50 am - 11:20 pm
MDW
-
PWM
12h 30m
2 stops
$234Delta
Thu, Feb 26 - Mon, Mar 2
Delta Logo
6:00 am - 12:46 pm
PWM
-
MDW
7h 46m
2 stops
Delta Logo
1:29 pm - 11:20 pm
MDW
-
PWM
8h 51m
2 stops
$239Delta
Thu, Feb 26 - Mon, Mar 2

Southwest flights from New Hampshire to Chicago Midway Airport

Our best Southwest deals on New Hampshire to Chicago Midway Airport flight tickets
Southwest
May 1
BOS3:45 pmBoston Logan Intl
2h 45m
MDW5:30 pmChicago Midway
May 4
MDW7:00 pmChicago Midway
2h 20m
BOS10:20 pmBoston Logan Intl
$132
Southwest
Mar 4
BOS5:30 amBoston Logan Intl
2h 50m
MDW7:20 amChicago Midway
Mar 7
MDW7:40 amChicago Midway
2h 15m
BOS10:55 amBoston Logan Intl
$133
Southwest
Feb 28
BOS2:10 pmBoston Logan Intl
6h 15m
1 stop
MDW7:25 pmChicago Midway
Mar 2
MDW6:35 pmChicago Midway
2h 15m
BOS9:50 pmBoston Logan Intl
$134

Delta flights from New Hampshire to Chicago Midway Airport

Our best Delta deals on New Hampshire to Chicago Midway Airport flight tickets
Delta
Feb 26
PWM5:31 amPortland
7h 28m
1 stop
MDW11:59 amChicago Midway
Mar 2
MDW9:50 amChicago Midway
12h 30m
2 stops
PWM11:20 pmPortland
$234
Delta
Feb 26
PWM6:00 amPortland
7h 46m
2 stops
MDW12:46 pmChicago Midway
Mar 3
MDW12:45 pmChicago Midway
10h 33m
2 stops
PWM12:18 amPortland
$239
Delta
Apr 9
PWM12:51 pmPortland
6h 03m
1 stop
MDW5:54 pmChicago Midway
Apr 13
MDW12:53 pmChicago Midway
10h 53m
2 stops
PWM12:46 amPortland
$254

momondo Fare Finder

 
Customize your flight search to find flights from New Hampshire to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 7, 2026.
Use the filters below to find and compare flights from New Hampshire to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 5/1

3:45 pm-5:30 pm

Nonstop2h 45m

Chicago Midway

Mon 5/4

7:00 pm-10:20 pm

Nonstop2h 20m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 3/4

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sat 3/7

7:40 am-10:55 am

Nonstop2h 15m

$133

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 3/9

3:10 pm-4:55 pm

Nonstop2h 45m

Chicago Midway

Thu 3/12

3:30 pm-6:45 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 4/10

6:55 pm-8:45 pm

Nonstop2h 50m

Chicago Midway

Sun 4/12

7:40 am-10:55 am

Nonstop2h 15m

$142

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 2/25

5:50 pm-1:56 pm

1 stop21h 06m

Chicago Midway

Thu 2/26

5:16 pm-1:13 am

1 stop6h 57m

$145

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 2/18

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Wed 2/18

5:35 pm-8:50 pm

Nonstop2h 15m

$146

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 2/26

6:00 am-4:16 pm

1 stop11h 16m

Chicago Midway

Mon 3/2

2:19 pm-1:13 am

1 stop9h 54m

$148

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 2/25

5:50 pm-1:56 pm

1 stop21h 06m

Chicago Midway

Mon 3/2

2:19 pm-4:45 pm

2 stops25h 26m

$149

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 2/26

5:31 am-11:59 am

1 stop7h 28m

Chicago Midway

Mon 3/2

9:50 am-11:20 pm

2 stops12h 30m

$234

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 2/26

6:00 am-12:46 pm

2 stops7h 46m

Chicago Midway

Mon 3/2

1:29 pm-11:20 pm

2 stops8h 51m

$239

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from New Hampshire to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from New Hampshire, with most prices found around $137. If you are unable to visit Chicago Midway Airport during the month of December, then departing from New Hampshire during the month January is also very affordable. Most momondo users find prices during this month for around $183.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from New Hampshire. The lowest ticket price found for a Wednesday departure recently was $282. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from New Hampshire because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $401.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from New Hampshire in the evening is the least expensive time of day to depart. momondo users have found prices as low as $266 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $350. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest New Hampshire to Chicago Midway flight route?

Fly from Manchester to Chicago Midway for the best New Hampshire - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from New Hampshire when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $256 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from New Hampshire for as low as $161 on momondo.

What cabin class options are available on New Hampshire to Chicago Midway flights?

There is only 1 cabin class available to choose from on New Hampshire to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap New Hampshire to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New Hampshire to Chicago Midway Airport

Best Price Found

$192

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from New Hampshire in the past 72 hours is $192. The best round-trip flight deal from New Hampshire to Chicago Midway Airport found on momondo in the last 72 hours is $424.
The fastest flight from New Hampshire to Chicago Midway Airport takes 2h 20m
Direct flights go from New Hampshire to Chicago Midway Airport every day.
Search flight deals

  • When did momondo last update prices for flights from New Hampshire to Chicago Midway Airport?

    Prices for flights from New Hampshire to Chicago Midway Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from New Hampshire to Chicago Midway Airport?

  • How old do you have to be to fly from New Hampshire to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from New Hampshire to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from New Hampshire to Chicago Midway Airport?

Best airlines flying from New Hampshire to Chicago Midway Airport

Compare and see reviews for airlines that fly from New Hampshire to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $196Free CancellationRating
8.0
4,280 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from New Hampshire to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from New Hampshire to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from New Hampshire to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from New Hampshire on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from New Hampshire to Chicago?

Once all potential New Hampshire to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from New Hampshire to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from New Hampshire and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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