$125 Cheap Flights from Montrose (MTJ) to Chicago (MDW)

View $125 flight on Wed, Oct 15, 2025Opens in a new window

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

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Cheap Flights from Montrose to Chicago (MTJ-MDW)

Prices were available within the past 7 days and start at $125 for one-way flights and $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Oct 15 - Mon, Oct 20
MTJ
Montrose
MDW
Chicago
$249 Roundtrip, found 15 hours ago
$249
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Montrose to Chicago, returning Mon, Oct 20, priced at $249 found 15 hours ago
Southwest Airlines
Thu, Oct 9 - Mon, Oct 13
MTJ
Montrose
MDW
Chicago
$254 Roundtrip, found 5 days ago
$254
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Oct 9 from Montrose to Chicago, returning Mon, Oct 13, priced at $254 found 5 days ago
Southwest Airlines
Thu, Aug 28 - Sun, Aug 31
MTJ
Montrose
MDW
Chicago
$294 Roundtrip, found 3 days ago
$294
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Aug 28 from Montrose to Chicago, returning Sun, Aug 31, priced at $294 found 3 days ago
Southwest Airlines
Wed, Oct 15 - Mon, Oct 20
MTJ
Montrose
MDW
Chicago
$299 Roundtrip, found 15 hours ago
$299
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Montrose to Chicago, returning Mon, Oct 20, priced at $299 found 15 hours ago
Southwest Airlines
Wed, Oct 15 - Mon, Oct 20
MTJ
Montrose
MDW
Chicago
$299 Roundtrip, found 15 hours ago
$299
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Montrose to Chicago, returning Mon, Oct 20, priced at $299 found 15 hours ago
Southwest Airlines
Wed, Oct 15 - Mon, Oct 20
MTJ
Montrose
MDW
Chicago
$329 Roundtrip, found 15 hours ago
$329
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Montrose to Chicago, returning Mon, Oct 20, priced at $329 found 15 hours ago
Southwest Airlines
Thu, Oct 9 - Mon, Oct 13
MTJ
Montrose
MDW
Chicago
$334 Roundtrip, found 5 days ago
$334
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Oct 9 from Montrose to Chicago, returning Mon, Oct 13, priced at $334 found 5 days ago
Southwest Airlines
Thu, Oct 9 - Mon, Oct 13
MTJ
Montrose
MDW
Chicago
$335 Roundtrip, found 5 days ago
$335
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Oct 9 from Montrose to Chicago, returning Mon, Oct 13, priced at $335 found 5 days ago
Southwest Airlines
Wed, Oct 15 - Mon, Oct 20
MTJ
Montrose
MDW
Chicago
$339 Roundtrip, found 1 day ago
$339
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Montrose to Chicago, returning Mon, Oct 20, priced at $339 found 1 day ago
Delta
Sun, Feb 8 - Wed, Feb 11
MTJ
Montrose
MDW
Chicago
$799 Roundtrip, found 5 days ago
$799
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Feb 8 from Montrose to Chicago, returning Wed, Feb 11, priced at $799 found 5 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 $434
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $434
Flights from Montrose (MTJ) to Chicago (MDW)
Origin airport
Montrose Regional
Destination airport
Midway Intl.
Airlines serving
Southwest Airlines
Roundtrip price
$248
Distance
1085 mi

Montrose to Chicago Flights

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

 

The best time to book a flight from Montrose to Chicago

Sunday is one of the best days to book for cheap flights from Montrose 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 Montrose 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 Montrose to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $125 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 Montrose 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 Montrose 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 Montrose Regional Airport (MTJ) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from MTJ 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 MTJ to MDW?
The cheapest flights from MTJ 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 MTJ to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MTJ to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Montrose Regional Airport (MTJ) to Midway Intl. Airport (MDW)?
There are no daily nonstop flights available from Montrose Regional Airport (MTJ) to Midway Intl. Airport (MDW). But you can opt for flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be cruising above the clouds before you know it.
What day of the week has the most flights from MTJ to MDW?
Usually you'll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* But this can vary depending on the airline, season 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 Montrose Regional Airport (MTJ) to Midway Intl. Airport (MDW)?
To reach Midway Intl. Airport (MDW) on time, pick a flight that leaves from Montrose Regional Airport (MTJ) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**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 Montrose Regional Airport (MTJ)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Montrose Regional Airport (MTJ). Explore the options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Montrose Regional Airport (MTJ) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your departure to book a ticket from MTJ to MDW generally means paying more. While you may come across some last-minute discounts, they aren't always guaranteed. Keep your travel plans flexible to boost your chances of landing a bargain.
Is it cheaper to book a MTJ to MDW flight and hotel package?
Booking a MTJ to MDW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Choose from our wide range of stays and then add activities, flights and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Montrose Regional Airport (MTJ) to Midway Intl. Airport (MDW)?
It's usually possible to reschedule or cancel your MTJ to MDW flight. However, if the booking was made more than 24 hours ago, additional charges 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.