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Cheap flights from Chicago to Boston from $165

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Boston departing on 5/24. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:05 pm - 9:15 pm
MDW
-
MHT
2h 10mnonstop
Southwest Logo
6:55 am - 8:20 am
MHT
-
MDW
2h 25mnonstop
$329Southwest
Wed, Jun 10 - Wed, Jun 17
American Airlines Logo
8:00 pm - 11:30 pm
ORD
-
MHT
2h 30mnonstop
American Airlines Logo
6:28 pm - 8:40 pm
MHT
-
ORD
3h 12mnonstop
$329American Airlines
Wed, Jul 22 - Tue, Jul 28
American Airlines Logo
8:00 pm - 11:30 pm
ORD
-
MHT
2h 30mnonstop
American Airlines Logo
6:00 am - 12:53 pm
MHT
-
ORD
7h 53m
1 stop
$339American Airlines
Wed, Jul 22 - Tue, Jul 28
Southwest Logo
6:05 pm - 9:15 pm
MDW
-
MHT
2h 10mnonstop
Southwest Logo
3:55 pm - 9:35 pm
MHT
-
MDW
6h 40m
1 stop
$339Southwest
Wed, Jun 10 - Wed, Jun 17
American Airlines Logo
8:13 pm - 11:46 pm
ORD
-
MHT
2h 33mnonstop
American Airlines Logo
7:00 am - 9:00 am
MHT
-
ORD
3h 00mnonstop
$344American Airlines
Thu, May 28 - Tue, Jun 2
Southwest Logo
3:45 pm - 6:50 pm
MDW
-
MHT
2h 05mnonstop
Southwest Logo
8:45 am - 10:15 am
MHT
-
MDW
2h 30mnonstop
$344Southwest
Sat, May 23 - Sun, May 24
American Airlines Logo
8:00 am - 4:40 pm
ORD
-
MHT
7h 40m
1 stop
American Airlines Logo
6:00 am - 12:53 pm
MHT
-
ORD
7h 53m
1 stop
$349American Airlines
Wed, Jul 22 - Tue, Jul 28
Southwest Logo
5:25 pm - 11:05 pm
MDW
-
MHT
4h 40m
1 stop
Southwest Logo
8:45 am - 10:15 am
MHT
-
MDW
2h 30mnonstop
$354Southwest
Sat, May 23 - Sun, May 24
American Airlines Logo
5:57 am - 11:33 am
ORD
-
MHT
4h 36m
1 stop
American Airlines Logo
12:20 pm - 2:15 pm
MHT
-
ORD
2h 55mnonstop
$354American Airlines
Thu, May 28 - Tue, Jun 2
United Airlines Logo
6:30 am - 2:08 pm
ORD
-
MHT
6h 38m
1 stop
United Airlines Logo
7:41 pm - 11:40 pm
MHT
-
ORD
4h 59m
1 stop
$384United Airlines
Wed, Aug 19 - Mon, Aug 24

Southwest flights from Chicago to Manchester, New Hampshire

Our best Southwest deals on Chicago to Manchester, New Hampshire flight tickets
Southwest
Jun 10
MDW6:05 pmChicago Midway
2h 10m
MHT9:15 pmManchester
Jun 17
MHT6:55 amManchester
2h 25m
MDW8:20 amChicago Midway
$329
Southwest
Jun 10
MDW6:05 pmChicago Midway
2h 10m
MHT9:15 pmManchester
Jun 17
MHT3:55 pmManchester
6h 40m
1 stop
MDW9:35 pmChicago Midway
$339
Southwest
May 23
MDW3:45 pmChicago Midway
2h 05m
MHT6:50 pmManchester
May 24
MHT8:45 amManchester
2h 30m
MDW10:15 amChicago Midway
$344

American Airlines flights from Chicago to Manchester, New Hampshire

Our best American Airlines deals on Chicago to Manchester, New Hampshire flight tickets
American Airlines
Jul 22
ORD8:00 pmChicago O'Hare Intl
2h 30m
MHT11:30 pmManchester
Jul 28
MHT6:28 pmManchester
3h 12m
ORD8:40 pmChicago O'Hare Intl
$329
American Airlines
Jul 22
ORD8:00 pmChicago O'Hare Intl
2h 30m
MHT11:30 pmManchester
Jul 28
MHT6:00 amManchester
7h 53m
1 stop
ORD12:53 pmChicago O'Hare Intl
$339
American Airlines
May 28
ORD8:13 pmChicago O'Hare Intl
2h 33m
MHT11:46 pmManchester
Jun 2
MHT7:00 amManchester
3h 00m
ORD9:00 amChicago O'Hare Intl
$344

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Manchester, New Hampshire 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 May 13, 2026.
Use the filters below to find and compare flights from Chicago to Manchester, New Hampshire that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Wed 6/10

6:05 pm-9:15 pm

Nonstop2h 10m

Manchester

Wed 6/17

6:55 am-8:20 am

Nonstop2h 25m

$329

ChicagoManchester

ORD - MHT

ORDMHT

Chicago O'Hare Intl

Wed 7/22

8:00 pm-11:30 pm

Nonstop2h 30m

Manchester

Tue 7/28

6:28 pm-8:40 pm

Nonstop3h 12m

$329

ChicagoManchester

ORD - MHT

ORDMHT

Chicago O'Hare Intl

Wed 7/22

8:00 pm-11:30 pm

Nonstop2h 30m

Manchester

Tue 7/28

6:00 am-12:53 pm

1 stop7h 53m

$339

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Wed 6/10

6:05 pm-9:15 pm

Nonstop2h 10m

Manchester

Wed 6/17

3:55 pm-9:35 pm

1 stop6h 40m

$339

ChicagoManchester

ORD - MHT

ORDMHT

Chicago O'Hare Intl

Thu 5/28

8:13 pm-11:46 pm

Nonstop2h 33m

Manchester

Tue 6/2

7:00 am-9:00 am

Nonstop3h 00m

$344

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Sat 5/23

3:45 pm-6:50 pm

Nonstop2h 05m

Manchester

Sun 5/24

8:45 am-10:15 am

Nonstop2h 30m

$344

ChicagoManchester

ORD - MHT

ORDMHT

Chicago O'Hare Intl

Wed 7/22

8:00 am-4:40 pm

1 stop7h 40m

Manchester

Tue 7/28

6:00 am-12:53 pm

1 stop7h 53m

$349

ChicagoManchester

MDW - MHT

MDWMHT

Chicago Midway

Sat 5/23

5:25 pm-11:05 pm

1 stop4h 40m

Manchester

Sun 5/24

8:45 am-10:15 am

Nonstop2h 30m

$354

ChicagoManchester

ORD - MHT

ORDMHT

Chicago O'Hare Intl

Thu 5/28

5:57 am-11:33 am

1 stop4h 36m

Manchester

Tue 6/2

12:20 pm-2:15 pm

Nonstop2h 55m

$354

ChicagoManchester

ORD - MHT

ORDMHT

Chicago O'Hare Intl

Wed 8/19

6:30 am-2:08 pm

1 stop6h 38m

Manchester

Mon 8/24

7:41 pm-11:40 pm

1 stop4h 59m

$384

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 Boston from

How to get the cheapest flight ticket from Chicago to Manchester, New Hampshire

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 typical price of a round-trip flight between Chicago and Manchester, New Hampshire?

What is the cheapest month to fly to Manchester, New Hampshire?

If you aren’t able to travel during the month of September, then book flights to Manchester, New Hampshire from Chicago during July instead. Flights to Manchester, New Hampshire in July, while not as cheap as those in September, still average around $117.

What is the cheapest day to depart on your flight to Manchester, New Hampshire?

Our data shows that Saturday is the least expensive day to fly to Manchester, New Hampshire. Tickets to fly out on this day can be as low as $313. Be sure to avoid booking your departure on a Friday as prices are generally higher than usual. According to our data, the average ticket price to Manchester, New Hampshire on Friday is $469.

What is the cheapest time of day to depart on your flight to Manchester, New Hampshire?

Our most recent data shows that the best time of day to fly to Manchester, New Hampshire is in the afternoon. Flights from Chicago to Manchester, New Hampshire during this time can be as low as $327. Flights at noon are often more expensive with an average ticket price of $399.

What is the cheapest Chicago to Manchester flight route?

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

Can stopping save me money on Chicago to Manchester, New Hampshire flights?

No. A direct flight is the cheapest option for a flight between Chicago to Manchester, New Hampshire.

How have Chicago to Manchester, New Hampshire flight prices changed over time?

As of May 2026, prices for Chicago to Manchester, New Hampshire flights are approximately 21% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Manchester, New Hampshire

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Manchester, New Hampshire according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Manchester, New Hampshire (CHI to MHT) flight deals and tips

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

Best Price Found

$234

Fastest flight time

2h 05m

Direct flights

Every day

Airports in Manchester, New Hampshire

1 airport
The best one-way flight to Manchester, New Hampshire from Chicago in the past 72 hours is $234. The best round-trip flight deal from Chicago to Manchester, New Hampshire found on momondo in the last 72 hours is $399.
The fastest flight from Chicago to Manchester, New Hampshire takes 2h 05m
Direct flights go from Chicago to Manchester, New Hampshire every day.
There is 1 airport in Manchester, New Hampshire. From Chicago there are direct flights to Manchester (MHT).
Search flight deals

Frequently asked questions about flying from Chicago to Manchester, New Hampshire

  • How far is Chicago to Manchester by plane?

    Manchester is 826.5 mi away from Chicago. Flights usually cover this in 2h 05m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago to Manchester Airport?

    Prices for flights from Chicago to Manchester Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago to Manchester Airport?

  • How old do you have to be to fly from Chicago to Manchester 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 Chicago to Manchester Airport.

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

    The required travel and health documents for your Manchester Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Manchester Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago to Manchester, New Hampshire?

  • What is the most popular airline from Chicago to Manchester, New Hampshire?

Best airlines flying from Chicago to Manchester, New Hampshire

Compare and see reviews for airlines that fly from Chicago to Manchester, New Hampshire with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $181Free CancellationRating
7.9
4,296 reviews
Search Southwest flights
American AirlinesPriceFrom $181Free CancellationRating
7.1
11,662 reviews
Search American Airlines flights

  • Southwest Flights From Chicago to Manchester, New Hampshire

    Across 8 Southwest flights from Chicago to Manchester, New Hampshire this week, the average price was $429, with the best Southwest deals starting from $181 round-trip. 4,296 users have rated Southwest on momondo, with an average score of 7.9/10.

  • American Airlines Flights From Chicago to Manchester, New Hampshire

    The best American Airlines deal for Chicago to Manchester, New Hampshire flight tickets found on momondo in the last 72 hours was $181, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $428 round-trip. American Airlines operates 21 flights out of Chicago into Manchester, New Hampshire in an average week, so prices vary by time and availability. 11,662 American Airlines reviews by users on momondo have scored the airline at 7.1/10.

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Keene

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Manchester for you.

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

Flights from Chicago to Manchester with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Manchester?

momondo provides multiple filters to help you find the best flight to Manchester from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Manchester from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Manchester, New Hampshire trip

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