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Cheap flights from Chicago to Boston from $149

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Boston

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:10 pm - 9:20 pmMDW  Chicago Midway-MHT Manchester
2h 10mnonstop
Southwest Logo
5:50 pm - 7:30 pmMHT  Manchester-MDW Chicago Midway
2h 40mnonstop
$297Southwest
Mon, Nov 16 - Wed, Nov 18
Southwest Logo
5:55 pm - 9:10 pmMDW  Chicago Midway-MHT Manchester
2h 15mnonstop
Southwest Logo
7:40 am - 9:15 amMHT  Manchester-MDW Chicago Midway
2h 35mnonstop
$297Southwest
Wed, Oct 21 - Tue, Oct 27
American Airlines Logo
8:40 pm - 12:13 amORD  Chicago O'Hare Intl-MHT Manchester
2h 33mnonstop
American Airlines Logo
5:05 pm - 7:06 pmMHT  Manchester-ORD Chicago O'Hare Intl
3h 01mnonstop
$297American Airlines
Mon, Oct 19 - Wed, Oct 21
American Airlines Logo
8:40 pm - 12:13 amORD  Chicago O'Hare Intl-MHT Manchester
2h 33mnonstop
American Airlines Logo
5:05 pm - 7:06 pmMHT  Manchester-ORD Chicago O'Hare Intl
3h 01mnonstop
$297American Airlines
Mon, Oct 19 - Thu, Oct 22
American Airlines Logo
1:10 pm - 4:35 pmORD  Chicago O'Hare Intl-MHT Manchester
2h 25mnonstop
American Airlines Logo
7:07 am - 9:05 amMHT  Manchester-ORD Chicago O'Hare Intl
2h 58mnonstop
$297American Airlines
Wed, Oct 21 - Tue, Oct 27
American Airlines Logo
8:40 pm - 12:13 amORD  Chicago O'Hare Intl-MHT Manchester
2h 33mnonstop
American Airlines Logo
7:07 am - 9:05 amMHT  Manchester-ORD Chicago O'Hare Intl
2h 58mnonstop
$297American Airlines
Thu, Oct 22 - Thu, Oct 29
Southwest Logo
6:10 pm - 9:20 pmMDW  Chicago Midway-MHT Manchester
2h 10mnonstop
Southwest Logo
5:50 pm - 7:30 pmMHT  Manchester-MDW Chicago Midway
2h 40mnonstop
$297Southwest
Thu, Dec 3 - Mon, Dec 7
Southwest Logo
6:45 pm - 9:55 pmMDW  Chicago Midway-MHT Manchester
2h 10mnonstop
Southwest Logo
5:50 pm - 7:15 pmMHT  Manchester-MDW Chicago Midway
2h 25mnonstop
$297Southwest
Thu, Oct 15 - Wed, Oct 21
United Airlines Logo
5:59 am - 2:03 pmORD  Chicago O'Hare Intl-MHT Manchester
7h 04m1 stop Washington, D.C. Reagan-National
United Airlines Logo
2:38 pm - 6:54 pmMHT  Manchester-ORD Chicago O'Hare Intl
5h 16m1 stop Washington, D.C. Dulles Intl
$417United Airlines
Thu, Nov 5 - Tue, Nov 10
United Airlines Logo
12:55 pm - 7:01 pmORD  Chicago O'Hare Intl-MHT Manchester
5h 06m1 stop Washington, D.C. Dulles Intl
United Airlines Logo
2:50 pm - 9:29 pmMHT  Manchester-ORD Chicago O'Hare Intl
7h 39m1 stop Washington, D.C. Dulles Intl
$417United Airlines
Tue, Oct 20 - Wed, Oct 21

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Southwest flights from Chicago to Manchester, New Hampshire

Our best Southwest deals on Chicago to Manchester, New Hampshire flight tickets
Southwest
Oct 15
MDW6:45 pmChicago Midway
2h 10m
MHT9:55 pmManchester
Oct 21
MHT5:50 pmManchester
2h 25m
MDW7:15 pmChicago Midway
$297
Southwest
Oct 21
MDW4:45 pmChicago Midway
5h 00m
1 stop
MHT10:45 pmManchester
Oct 27
MHT5:50 pmManchester
2h 25m
MDW7:15 pmChicago Midway
$307
Southwest
Oct 15
MDW6:45 pmChicago Midway
2h 10m
MHT9:55 pmManchester
Oct 21
MHT6:45 amManchester
7h 40m
2 stops
MDW1:25 pmChicago Midway
$312

American Airlines flights from Chicago to Manchester, New Hampshire

Our best American Airlines deals on Chicago to Manchester, New Hampshire flight tickets
American Airlines
Oct 19
ORD8:40 pmChicago O'Hare Intl
2h 33m
MHT12:13 amManchester
Oct 21
MHT5:05 pmManchester
3h 01m
ORD7:06 pmChicago O'Hare Intl
$297
American Airlines
Oct 15
ORD1:10 pmChicago O'Hare Intl
2h 25m
MHT4:35 pmManchester
Oct 19
MHT5:24 pmManchester
7h 12m
1 stop
ORD11:36 pmChicago O'Hare Intl
$307
American Airlines
Oct 16
ORD8:40 pmChicago O'Hare Intl
2h 33m
MHT12:13 amManchester
Oct 20
MHT5:05 pmManchester
3h 01m
ORD7:06 pmChicago O'Hare Intl
$313

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago to Manchester, New Hampshire that are best for you.

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Route

Depart

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Price

Cheapest round-trip

ChicagoManchester

MDW Chicago Midway - MHT Manchester

MDWMHT

Chicago Midway

Mon 11/16

6:10 pm-9:20 pm

Nonstop2h 10m

Manchester

Wed 11/18

5:50 pm-7:30 pm

Nonstop2h 40m

$297

ChicagoManchester

MDW Chicago Midway - MHT Manchester

MDWMHT

Chicago Midway

Wed 10/21

5:55 pm-9:10 pm

Nonstop2h 15m

Manchester

Tue 10/27

7:40 am-9:15 am

Nonstop2h 35m

$297

ChicagoManchester

ORD Chicago O'Hare Intl - MHT Manchester

ORDMHT

Chicago O'Hare Intl

Mon 10/19

8:40 pm-12:13 am

Nonstop2h 33m

Manchester

Wed 10/21

5:05 pm-7:06 pm

Nonstop3h 01m

$297

ChicagoManchester

ORD Chicago O'Hare Intl - MHT Manchester

ORDMHT

Chicago O'Hare Intl

Mon 10/19

8:40 pm-12:13 am

Nonstop2h 33m

Manchester

Thu 10/22

5:05 pm-7:06 pm

Nonstop3h 01m

$297

ChicagoManchester

ORD Chicago O'Hare Intl - MHT Manchester

ORDMHT

Chicago O'Hare Intl

Wed 10/21

1:10 pm-4:35 pm

Nonstop2h 25m

Manchester

Tue 10/27

7:07 am-9:05 am

Nonstop2h 58m

$297

ChicagoManchester

ORD Chicago O'Hare Intl - MHT Manchester

ORDMHT

Chicago O'Hare Intl

Thu 10/22

8:40 pm-12:13 am

Nonstop2h 33m

Manchester

Thu 10/29

7:07 am-9:05 am

Nonstop2h 58m

$297

ChicagoManchester

MDW Chicago Midway - MHT Manchester

MDWMHT

Chicago Midway

Thu 12/3

6:10 pm-9:20 pm

Nonstop2h 10m

Manchester

Mon 12/7

5:50 pm-7:30 pm

Nonstop2h 40m

$297
Quickest round-trip

ChicagoManchester

MDW Chicago Midway - MHT Manchester

MDWMHT

Chicago Midway

Thu 10/15

6:45 pm-9:55 pm

Nonstop2h 10m

Manchester

Wed 10/21

5:50 pm-7:15 pm

Nonstop2h 25m

$297

ChicagoManchester

ORD Chicago O'Hare Intl - MHT Manchester

ORDMHT

Chicago O'Hare Intl

Thu 11/5

5:59 am-2:03 pm

1 stop7h 04m

Manchester

Tue 11/10

2:38 pm-6:54 pm

1 stop5h 16m

$417

ChicagoManchester

ORD Chicago O'Hare Intl - MHT Manchester

ORDMHT

Chicago O'Hare Intl

Tue 10/20

12:55 pm-7:01 pm

1 stop5h 06m

Manchester

Wed 10/21

2:50 pm-9:29 pm

1 stop7h 39m

$417

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

Prices are currently low for flights on this route.

Typical prices usually range from $445 to $509.
The lowest price recently found on this route was $297.

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

If you aren’t able to travel during the month of January, then book flights to Manchester, New Hampshire from Chicago during April instead. Flights to Manchester, New Hampshire in April, while not as cheap as those in January, still average around $387.

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 $357. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Manchester, New Hampshire on Sunday is $513.

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 $404. Flights in the evening are often more expensive with an average ticket price of $469.

What is the cheapest Chicago to Manchester flight route?

Fly from Chicago O'Hare Intl to Manchester for the best Chicago - Manchester flight prices

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

There are 3 cabin classes available to choose from on Chicago to Manchester, New Hampshire flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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 September 2026, prices for Chicago to Manchester, New Hampshire flights are approximately 20% cheaper 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

$149

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 $149. The best round-trip flight deal from Chicago to Manchester, New Hampshire found on momondo in the last 72 hours is $297.
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
American AirlinesPriceFrom $252Free CancellationRating
7.0
12,097 reviews
Search American Airlines flights
SouthwestPriceFrom $257Free CancellationRating
8.0
4,201 reviews
Search Southwest flights

  • Southwest Flights From Chicago to Manchester, New Hampshire

    Across 6 Southwest flights from Chicago to Manchester, New Hampshire this week, the average price was $372, with the best Southwest deals starting from $257 round-trip. 4,201 users have rated Southwest on momondo, with an average score of 8.0/10.

  • 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 $252, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $457 round-trip. American Airlines operates 17 flights out of Chicago into Manchester, New Hampshire in an average week, so prices vary by time and availability. 12,097 American Airlines reviews by users on momondo have scored the airline at 7.0/10.

Traveling to a place near Boston?

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