$91 Cheap Flights from Chicago (MDW) to Manchester (MHT)

View $91 flight on Tue, Aug 19, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Manchester-Boston Regional Airport (MHT)

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Cheap Flights from Chicago to Manchester (MDW-MHT)

Prices were available within the past 7 days and start at $91 for one-way flights and $105 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Mon, Aug 4 - Tue, Aug 5
MDW
Chicago
MHT
Manchester
$105 Roundtrip, found 2 days ago
$105
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Aug 4 from Chicago to Manchester, returning Tue, Aug 5, priced at $105 found 2 days ago
Southwest Airlines
Tue, Oct 14 - Wed, Oct 15
MDW
Chicago
MHT
Manchester
$106 Roundtrip, found 4 days ago
$106
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Oct 14 from Chicago to Manchester, returning Wed, Oct 15, priced at $106 found 4 days ago
Southwest Airlines
Thu, Aug 14 - Tue, Aug 19
MDW
Chicago
MHT
Manchester
$114 Roundtrip, found 4 days ago
$114
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Aug 14 from Chicago to Manchester, returning Tue, Aug 19, priced at $114 found 4 days ago
Southwest Airlines
Tue, Dec 9 - Sat, Dec 13
MDW
Chicago
MHT
Manchester
$115 Roundtrip, found 2 days ago
$115
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Dec 9 from Chicago to Manchester, returning Sat, Dec 13, priced at $115 found 2 days ago
Southwest Airlines
Wed, Sep 17 - Sun, Sep 21
MDW
Chicago
MHT
Manchester
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Sep 17 from Chicago to Manchester, returning Sun, Sep 21, priced at $120 found 1 day ago
Southwest Airlines
Thu, Aug 14 - Tue, Aug 19
MDW
Chicago
MHT
Manchester
$123 Roundtrip, found 4 days ago
$123
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Aug 14 from Chicago to Manchester, returning Tue, Aug 19, priced at $123 found 4 days ago
Southwest Airlines
Tue, Dec 9 - Sat, Dec 13
MDW
Chicago
MHT
Manchester
$124 Roundtrip, found 2 days ago
$124
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Dec 9 from Chicago to Manchester, returning Sat, Dec 13, priced at $124 found 2 days ago
Southwest Airlines
Tue, Oct 7 - Wed, Oct 8
MDW
Chicago
MHT
Manchester
$125 Roundtrip, found 4 days ago
$125
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Oct 7 from Chicago to Manchester, returning Wed, Oct 8, priced at $125 found 4 days ago
Southwest Airlines
Tue, Dec 9 - Sat, Dec 13
MDW
Chicago
MHT
Manchester
$130 Roundtrip, found 2 days ago
$130
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Dec 9 from Chicago to Manchester, returning Sat, Dec 13, priced at $130 found 2 days ago
Southwest Airlines
Tue, Oct 7 - Wed, Oct 8
MDW
Chicago
MHT
Manchester
$131 Roundtrip, found 4 days ago
$131
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Oct 7 from Chicago to Manchester, returning Wed, Oct 8, priced at $131 found 4 days ago

Find the cheapest month to fly from Chicago (MDW) to Manchester (MHT)

August is typically the cheapest month to fly

From $141 - $2,294 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (MDW) to Manchester (MHT)
Origin airport
Midway Intl.
Destination airport
Manchester-Boston Regional
Airlines serving
Southwest Airlines
Roundtrip price
$105
Distance
834 mi
Average flight time
3 hours 7 mins

Chicago to Manchester Flights

The cheapest times to fly from Chicago to Manchester

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Manchester are during the month of August. You can find some of the cheapest flights from Chicago to Manchester with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Manchester

Sunday is one of the best days to book for cheap flights from Chicago to Manchester: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Manchester

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Manchester in 2025. You can also book with separate airlines for your outbound and return journeys, from $91 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Manchester flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Manchester airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT) cost?
Score cheap return flights from Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT) starting from $114. Grab a seat and take off on your trip. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving MDW on August 6 2025 and touching down at MHT. The price was last updated on July 10 2025 and has not changed since.
What is the cheapest month to fly from MDW to MHT?
The cheapest flights from MDW to MHT are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT)?
Hop on a nonstop flight with Southwest Airlines and head straight from Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT).
What is the cheapest airline that flies from MDW to MHT?
Jet off from MDW to MHT with Southwest Airlines. This airline currently offers the lowest one-way fare for this route, starting at $53. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on August 12 2025. Prices were last updated on July 10 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT)?
On average, you can choose from 6 direct flights each week from Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT). To increase your travel options, consider taking a flight with a layover. Just enter your dates on Expedia and then set the filters to include one or more stops.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT)?
Flights between MDW and MHT are their busiest at 6 PM. For a quieter trip and potentially cheaper tickets, look for a time outside the usual busy windows.
What day of the week has the most flights from MDW to MHT?
Depart on a Friday if you're looking for the best selection of flights from Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT).
What is the earliest flight from Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT)?
Midway Intl. Airport (MDW)'s earliest flight to Manchester-Boston Regional Airport (MHT) takes off at approximately 12:50PM UTC-6. With a total flight time of 2h, you'll arrive at around 3:50PM UTC-5.
How long does it take to fly from Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT)?
Flights from MDW to MHT have an average travel time of 2 hours and 3 minutes. The total distance between the two is 840 mi.
What airline has the least delays from MDW to MHT?
With 85% of flights usually arriving on time, Southwest Airlines has the best on-time performance for nonstop flights from Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT). To monitor your flight status and get notified about any changes, head to the Expedia App.
What is the best time to fly from Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT)?
To avoid potential delays on the Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT) route, fly before 3 PM. Departures after this time are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Manchester from Midway Intl. Airport (MDW)?
Board a direct flight from Midway Intl. Airport (MDW) to Manchester and touch down at Logan Intl. Airport (BOS). Another convenient arrival point to this destination is Manchester-Boston Regional Airport (MHT).
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT) last-minute?
Booking your ticket from MDW to MHT just before your getaway is usually more expensive. But if there's some wiggle room with your schedule, you could bag a cheap last-minute fare.
Is it cheaper to book a MDW to MHT flight and hotel package?
You'll typically save money by securing a MDW to MHT flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. Once you've selected your preferred flights and accommodations, consider adding extras including activities, tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Manchester-Boston Regional Airport (MHT)?
If you reserved your MDW to MHT flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you'd like more information.

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