$119 Cheap Flights from Missoula (MSO) to Chicago (MDW)

View $119 flight on Tue, Sep 23, 2025Opens in a new window

Popular airlines from Missoula Intl. Airport (MSO) to Chicago Midway Airport (MDW)

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Cheap Flights from Missoula to Chicago (MSO-MDW)

Prices were available within the past 7 days and start at $119 for one-way flights and $237 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Sep 24 - Mon, Sep 29
MSO
Missoula
MDW
Chicago
$237 Roundtrip, found 5 days ago
$237
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Sep 24 from Missoula to Chicago, returning Mon, Sep 29, priced at $237 found 5 days ago
Delta
Tue, Nov 18 - Wed, Dec 3
MSO
Missoula
MDW
Chicago
$274 Roundtrip, found 1 day ago
$274
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Nov 18 from Missoula to Chicago, returning Wed, Dec 3, priced at $274 found 1 day ago
Delta
Sat, Oct 18 - Wed, Oct 22
MSO
Missoula
MDW
Chicago
$279 Roundtrip, found 10 hours ago
$279
Roundtrip
found 10 hours ago
Select Delta flight, departing Sat, Oct 18 from Missoula to Chicago, returning Wed, Oct 22, priced at $279 found 10 hours ago
Delta
Tue, Nov 18 - Tue, Dec 2
MSO
Missoula
MDW
Chicago
$315 Roundtrip, found 1 day ago
$315
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Nov 18 from Missoula to Chicago, returning Tue, Dec 2, priced at $315 found 1 day ago
Delta
Wed, Sep 24 - Mon, Sep 29
MSO
Missoula
MDW
Chicago
$317 Roundtrip, found 5 days ago
$317
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Sep 24 from Missoula to Chicago, returning Mon, Sep 29, priced at $317 found 5 days ago
Delta
Tue, Nov 18 - Fri, Dec 5
MSO
Missoula
MDW
Chicago
$319 Roundtrip, found 1 day ago
$319
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Nov 18 from Missoula to Chicago, returning Fri, Dec 5, priced at $319 found 1 day ago
Delta
Wed, Aug 20 - Sat, Aug 23
MSO
Missoula
MDW
Chicago
$324 Roundtrip, found 13 hours ago
$324
Roundtrip
found 13 hours ago
Select Delta flight, departing Wed, Aug 20 from Missoula to Chicago, returning Sat, Aug 23, priced at $324 found 13 hours ago
Delta
Sat, Sep 27 - Sun, Sep 28
MSO
Missoula
MDW
Chicago
$325 Roundtrip, found 1 day ago
$325
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 27 from Missoula to Chicago, returning Sun, Sep 28, priced at $325 found 1 day ago
Frontier Airlines
Mon, Oct 13 - Thu, Oct 16
MSO
Missoula
MDW
Chicago
$326 Roundtrip, found 10 hours ago
$326
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Mon, Oct 13 from Missoula to Chicago, returning Thu, Oct 16, priced at $326 found 10 hours ago
Delta
Sat, Nov 22 - Wed, Dec 3
MSO
Missoula
MDW
Chicago
$329 Roundtrip, found 6 days ago
$329
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Nov 22 from Missoula to Chicago, returning Wed, Dec 3, priced at $329 found 6 days ago

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 $248
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $248
Flights from Missoula (MSO) to Chicago (MDW)
Origin airport
Missoula Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$236
Distance
1341 mi

Missoula to Chicago Flights

The cheapest times to fly from Missoula 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 Missoula to Chicago are during the month of September. You can find some of the cheapest flights from Missoula to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Missoula to Chicago

Sunday is one of the best days to book for cheap flights from Missoula 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 Missoula 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 Missoula to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $119 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 Missoula 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 Missoula 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 Missoula Intl. Airport (MSO) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from MSO to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MSO to MDW?
The cheapest flights from MSO to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MSO to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MSO to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Missoula Intl. Airport (MSO) to Midway Intl. Airport (MDW)?
There are no daily direct flights departing from Missoula Intl. Airport (MSO) to Midway Intl. Airport (MDW). But you can opt for flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be cruising above the clouds before you know it.
What day of the week has the most flights from MSO to MDW?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Missoula Intl. Airport (MSO) to Midway Intl. Airport (MDW)?
To reach Midway Intl. Airport (MDW) on time, opt for a flight that leaves Missoula Intl. Airport (MSO) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**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.
Is it cheaper to buy a plane ticket from Missoula Intl. Airport (MSO) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from MSO to MDW shortly before your getaway is typically more expensive. However, if you're flexible with your departure times and dates, you could land a cheap last-minute fare.
Is it cheaper to book a MSO to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a MSO to MDW flight and hotel package with Expedia could result in significant savings. What's more, managing everything in one place will take the hassle out of planning your trip. Just pick your flights and choose from our wide range of hotels, then tailor your trip with extras like car rentals and activities.
Can I cancel or change the date of my flight from Missoula Intl. Airport (MSO) to Midway Intl. Airport (MDW)?
It's usually possible to reschedule or cancel your MSO to MDW flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more information on our Customer Service portal.

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*Available to One Key members.