$145 Cheap Flights from Manchester (MHT) to Chicago (MDW)

View $145 flight on Sun, Jan 18, 2026Opens in a new window

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

Cheap Flights from Manchester to Chicago (MHT-MDW)

Prices were available within the past 7 days and start at $145 for one-way flights and $307 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Nov 22 - Mon, Nov 24
MHT
Manchester
MDW
Chicago
$307 Roundtrip, just found
$307
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Nov 22 from Manchester to Chicago, returning Mon, Nov 24, priced at $307 just found
Southwest Airlines
Tue, Dec 16 - Thu, Dec 18
MHT
Manchester
MDW
Chicago
$314 Roundtrip, found 4 hours ago
$314
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Manchester to Chicago, returning Thu, Dec 18, priced at $314 found 4 hours ago
Southwest Airlines
Mon, Feb 2 - Wed, Feb 4
MHT
Manchester
MDW
Chicago
$317 Roundtrip, found 2 days ago
$317
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Feb 2 from Manchester to Chicago, returning Wed, Feb 4, priced at $317 found 2 days ago
Southwest Airlines
Tue, Dec 16 - Thu, Dec 18
MHT
Manchester
MDW
Chicago
$324 Roundtrip, found 4 hours ago
$324
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Manchester to Chicago, returning Thu, Dec 18, priced at $324 found 4 hours ago
Southwest Airlines
Tue, Dec 16 - Thu, Dec 18
MHT
Manchester
MDW
Chicago
$326 Roundtrip, found 4 hours ago
$326
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Manchester to Chicago, returning Thu, Dec 18, priced at $326 found 4 hours ago
Southwest Airlines
Mon, Feb 2 - Wed, Feb 4
MHT
Manchester
MDW
Chicago
$327 Roundtrip, found 2 days ago
$327
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Feb 2 from Manchester to Chicago, returning Wed, Feb 4, priced at $327 found 2 days ago
Southwest Airlines
Mon, Feb 2 - Wed, Feb 4
MHT
Manchester
MDW
Chicago
$332 Roundtrip, found 2 days ago
$332
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Feb 2 from Manchester to Chicago, returning Wed, Feb 4, priced at $332 found 2 days ago
Southwest Airlines
Tue, Dec 16 - Thu, Dec 18
MHT
Manchester
MDW
Chicago
$336 Roundtrip, found 4 hours ago
$336
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Manchester to Chicago, returning Thu, Dec 18, priced at $336 found 4 hours ago
Southwest Airlines
Sat, Feb 7 - Mon, Feb 9
MHT
Manchester
MDW
Chicago
$338 Roundtrip, found 5 days ago
$338
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Feb 7 from Manchester to Chicago, returning Mon, Feb 9, priced at $338 found 5 days ago
Southwest Airlines
Tue, Dec 16 - Thu, Dec 18
MHT
Manchester
MDW
Chicago
$341 Roundtrip, found 4 hours ago
$341
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Manchester to Chicago, returning Thu, Dec 18, priced at $341 found 4 hours ago

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

September is typically the cheapest month to fly

From $129 - $869 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $561
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $561

Frequently asked questions

How much does a flight from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $145 or cheap return flight from $307 from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
Flying in November can help you save, as it's the cheapest month for flights between MHT and MDW. You'll typically find the lowest prices during off-peak months.
Which airlines fly direct from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
When heading out of Manchester-Boston Regional Airport (MHT), you can get on a direct flight to Midway Intl. Airport (MDW) with Southwest Airlines.
What is the cheapest airline that flies from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll take you from MHT to MDW. Then, sort your results by "Price (lowest to highest)" to pick up a good deal.
How many flights per day from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
On average, you can pick from 6 direct weekly flights from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW). To expand your choices, consider flights with layovers. Enter your details on Expedia and then filter your search results to show one stop or more.
What are the most popular departure times for flights from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
More people fly between MHT and MDW at 7 AM than at any other time of day. Rather skip the crowds? Pick a flight outside the busiest times and it's possible you'll save on your ticket as well.
What day of the week has the most flights from MHT to MDW?
Friday has the most flights from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW). Consider leaving on this day and you'll have a greater chance of finding a departure that fits your plans.
What is the earliest flight from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
The first flight of the day leaving from Manchester-Boston Regional Airport (MHT) is at around 7:15AM UTC-5. Catch this flight and you'll land at Midway Intl. Airport (MDW) at approximately 8:55AM UTC-6. The overall travel time is 2h 40m.
How long does it take to fly from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
It takes about 2 hours and 40 minutes to travel the 840 mi from MHT to MDW.
What is the best time to fly from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
Opt for a flight from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of delays and cancellations. Departures later than this have a 22% higher chance of being canceled, on average.**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 Chicago from Manchester-Boston Regional Airport (MHT)?
If you're traveling on a direct flight from Manchester-Boston Regional Airport (MHT) to Chicago, Midway Intl. Airport (MDW) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from MHT to MDW shortly before your getaway is usually more expensive. But if you're flexible with your itinerary, you could grab a cheap last-minute fare.
Is it cheaper to book a MHT to MDW flight and hotel package?
You'll typically save money by securing a MHT to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. Once you've selected your ideal flights and accommodations, you can add extras such as activities, tours and car rentals.
Can I cancel or change the date of my flight from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
Generally, it's possible to reschedule or cancel your MHT to MDW flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Manchester-Boston Regional
Destination airport
Midway Intl.
Airlines serving
Southwest Airlines
Roundtrip price
$307
Distance
834 mi
Average flight time
2 hours 30 mins

Book with confidence

Manchester to Chicago Flights

The cheapest times to fly from Manchester to Chicago

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 Manchester to Chicago are during the month of November. You can find some of the cheapest flights from Manchester to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Manchester to Chicago

Sunday is one of the best days to book for cheap flights from Manchester to Chicago: 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 Manchester to Chicago

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 Manchester to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $145 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 Manchester to Chicago 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 Manchester to Chicago 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.

 

Manchester to Chicago Flights

Explore a world of travel with Expedia

*Available to One Key members.