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

View $145 flight on Tue, Oct 14, 2025Opens 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 $289 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Oct 15 - Tue, Oct 21
MHT
Manchester
MDW
Chicago
$289 Roundtrip, found 12 hours ago
$289
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Manchester to Chicago, returning Tue, Oct 21, priced at $289 found 12 hours ago
Southwest Airlines
Wed, Oct 15 - Tue, Oct 21
MHT
Manchester
MDW
Chicago
$299 Roundtrip, found 12 hours ago
$299
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Manchester to Chicago, returning Tue, Oct 21, priced at $299 found 12 hours ago
Southwest Airlines
Wed, Oct 15 - Tue, Oct 21
MHT
Manchester
MDW
Chicago
$304 Roundtrip, found 12 hours ago
$304
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Manchester to Chicago, returning Tue, Oct 21, priced at $304 found 12 hours ago
Southwest Airlines
Wed, Oct 15 - Tue, Oct 21
MHT
Manchester
MDW
Chicago
$309 Roundtrip, found 12 hours ago
$309
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Manchester to Chicago, returning Tue, Oct 21, priced at $309 found 12 hours ago
Southwest Airlines
Wed, Oct 15 - Sat, Oct 18
MHT
Manchester
MDW
Chicago
$309 Roundtrip, found 2 hours ago
$309
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Manchester to Chicago, returning Sat, Oct 18, priced at $309 found 2 hours ago
Southwest Airlines
Wed, Oct 15 - Tue, Oct 21
MHT
Manchester
MDW
Chicago
$314 Roundtrip, found 12 hours ago
$314
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Manchester to Chicago, returning Tue, Oct 21, priced at $314 found 12 hours ago
Southwest Airlines
Wed, Oct 15 - Sat, Oct 18
MHT
Manchester
MDW
Chicago
$319 Roundtrip, found 2 hours ago
$319
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Manchester to Chicago, returning Sat, Oct 18, priced at $319 found 2 hours ago
Southwest Airlines
Thu, Jan 1 - Tue, Jan 6
MHT
Manchester
MDW
Chicago
$319 Roundtrip, found 1 day ago
$319
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Jan 1 from Manchester to Chicago, returning Tue, Jan 6, priced at $319 found 1 day ago
Southwest Airlines
Fri, Oct 31 - Mon, Nov 3
MHT
Manchester
MDW
Chicago
$323 Roundtrip, found 3 days ago
$323
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Manchester to Chicago, returning Mon, Nov 3, priced at $323 found 3 days ago
Southwest Airlines
Wed, Oct 15 - Sat, Oct 18
MHT
Manchester
MDW
Chicago
$324 Roundtrip, found 2 hours ago
$324
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Manchester to Chicago, returning Sat, Oct 18, priced at $324 found 2 hours ago

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

September is typically the cheapest month to fly

From $135 - $1,378 per traveler.

Graph displaying average flight prices per month

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 $462
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $462
Flights from Manchester (MHT) to Chicago (MDW)
Origin airport
Manchester-Boston Regional
Destination airport
Midway Intl.
Airlines serving
Southwest Airlines
Roundtrip price
$289
Distance
834 mi
Average flight time
2 hours 43 mins

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 October. 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.

 

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 $289 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 October 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.

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*Available to One Key members.