$105 Cheap Flights from Chicago (MDW) to Montrose (MTJ)

View $105 flight on Tue, Nov 4, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Montrose Regional Airport (MTJ)

Cheap Flights from Chicago to Montrose (MDW-MTJ)

Prices were available within the past 7 days and start at $105 for one-way flights and $209 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Nov 4 - Mon, Nov 10
MDW
Chicago
MTJ
Montrose
$209 Roundtrip, found 6 days ago
$209
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Nov 4 from Chicago to Montrose, returning Mon, Nov 10, priced at $209 found 6 days ago
Southwest Airlines
Tue, Nov 4 - Mon, Nov 10
MDW
Chicago
MTJ
Montrose
$259 Roundtrip, found 6 days ago
$259
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Nov 4 from Chicago to Montrose, returning Mon, Nov 10, priced at $259 found 6 days ago
Southwest Airlines
Tue, Nov 4 - Mon, Nov 10
MDW
Chicago
MTJ
Montrose
$269 Roundtrip, found 6 days ago
$269
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Nov 4 from Chicago to Montrose, returning Mon, Nov 10, priced at $269 found 6 days ago
Southwest Airlines
Tue, Nov 4 - Mon, Nov 10
MDW
Chicago
MTJ
Montrose
$289 Roundtrip, found 6 days ago
$289
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Nov 4 from Chicago to Montrose, returning Mon, Nov 10, priced at $289 found 6 days ago
Southwest Airlines
Wed, Oct 29 - Wed, Nov 5
MDW
Chicago
MTJ
Montrose
$309 Roundtrip, found 2 days ago
$309
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Montrose, returning Wed, Nov 5, priced at $309 found 2 days ago
Southwest Airlines
Wed, Oct 29 - Wed, Nov 5
MDW
Chicago
MTJ
Montrose
$314 Roundtrip, found 2 days ago
$314
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Montrose, returning Wed, Nov 5, priced at $314 found 2 days ago
Southwest Airlines
Fri, Nov 7 - Mon, Nov 10
MDW
Chicago
MTJ
Montrose
$320 Roundtrip, found 4 days ago
$320
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Nov 7 from Chicago to Montrose, returning Mon, Nov 10, priced at $320 found 4 days ago
Delta
Fri, Jan 2 - Fri, Jan 16
MDW
Chicago
MTJ
Montrose
$324 Roundtrip, found 2 days ago
$324
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Jan 2 from Chicago to Montrose, returning Fri, Jan 16, priced at $324 found 2 days ago
Southwest Airlines
Fri, Jan 2 - Sat, Jan 10
MDW
Chicago
MTJ
Montrose
$329 Roundtrip, found 4 days ago
$329
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Jan 2 from Chicago to Montrose, returning Sat, Jan 10, priced at $329 found 4 days ago
Southwest Airlines
Wed, Oct 29 - Wed, Nov 5
MDW
Chicago
MTJ
Montrose
$329 Roundtrip, found 2 days ago
$329
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Montrose, returning Wed, Nov 5, priced at $329 found 2 days ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Montrose Regional Airport (MTJ) cost?
Grab a cheap one-way flight from $105 or cheap return flight from $209 from Midway Intl. Airport (MDW) to Montrose Regional Airport (MTJ) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Montrose Regional Airport (MTJ)?
Planning your trip for November is a good way to save, as it's the cheapest month for flights between MDW and MTJ. You'll usually find the lowest fares during off-peak months.
Which airlines fly direct from Midway Intl. Airport (MDW) to Montrose Regional Airport (MTJ)?
There are no direct flights from Chicago, IL (MDW-Midway Intl.) to Montrose Regional Airport (MTJ). However, you can find other airports that offer nonstop flights. Begin your journey at O'Hare Intl. Airport (ORD) and fly straight to Montrose without a layover.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Montrose Regional Airport (MTJ)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest MDW to MTJ flight.
How many flights per day from Midway Intl. Airport (MDW) to Montrose Regional Airport (MTJ)?
Direct flights from Midway Intl. Airport (MDW) to Montrose Regional Airport (MTJ) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel details and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to MTJ?
Usually you'll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* However, this can change depending on the season, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Montrose Regional Airport (MTJ)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Montrose Regional Airport (MTJ) route, travel before 3 PM. Later departures 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.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Montrose Regional Airport (MTJ) last-minute?
Booking your plane ticket from MDW to MTJ just before your getaway is usually more expensive. But if you're flexible with your schedule, you could score a cheap last-minute fare.
Is it cheaper to book a MDW to MTJ flight and hotel package?
You can save money by securing a MDW to MTJ flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. After choosing your preferred accommodations and flights, consider adding extras such as car rentals, tours and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Montrose Regional Airport (MTJ)?
Usually, it's possible to cancel or reschedule your MDW to MTJ 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 allowed and if any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Montrose Regional
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$208
Distance
1085 mi

Book with confidence

Book with confidence

Chicago to Montrose Flights

The cheapest times to fly from Chicago to Montrose

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

 

The best time to book a flight from Chicago to Montrose

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

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 Montrose in 2025. You can also book with separate airlines for your outbound and return journeys, from $105 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 Montrose 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 Montrose 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.

 

Chicago to Montrose Flights

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*Available to One Key members.