HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$275+ Cheap flights from Montrose (MTJ) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
MTJ — MDW
Oct 26 — Nov 21
Sun 10/26
Sun 11/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Montrose to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Montrose to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Montrose (MTJ) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$289
(Southwest)

One-way from

$275
(Southwest)

Popular in

December

Cheapest in

September

Average price

$256
Provider with most accurate pricing for Montrose County-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montrose County-Chicago Midway flights.
Search Deals
From Montrose County to Chicago Midway
Search Deals
One-way flight from Montrose County to Chicago Midway
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Montrose to Midway

Cheapest flights from Montrose to Midway
Explore the most affordable flight options available from Montrose to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 26, 2025.

This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2511:25 amMTJ - MDW
1 stop8h 20mSouthwest
Mon 10/277:55 amMDW - MTJ
1 stop6h 05mSouthwest
Deal found 9/25$289
This Southwest deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/711:50 amMTJ - MDW
1 stop7h 25mSouthwest
Mon 11/109:50 pmMDW - MTJ
2 stops14h 30mSouthwest
Deal found 9/24$295
This Southwest deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/111:25 amMTJ - MDW
2 stops7h 55mSouthwest
Mon 11/35:00 amMDW - MTJ
2 stops7h 20mSouthwest
Deal found 9/24$345

Cheapflights Fare Finder

 
Customize your flight search to find flights from Montrose to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 26, 2025.
Use the filters below to find and compare flights from Montrose to Chicago Midway Airport that are best for you.

Fly from

Montrose

Fly to

Midway

Route

Depart

Return

Price

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Sat 10/25

11:25 am-8:45 pm

1 stop8h 20m

Chicago Midway

Mon 10/27

7:55 am-1:00 pm

1 stop6h 05m

$289

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Sat 11/1

11:25 am-8:20 pm

2 stops7h 55m

Chicago Midway

Mon 11/3

5:30 am-11:20 am

1 stop6h 50m

$289

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Fri 11/7

11:50 am-8:15 pm

1 stop7h 25m

Chicago Midway

Mon 11/10

9:50 pm-11:20 am

2 stops14h 30m

$295

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Sun 2/22

3:50 pm-11:10 pm

1 stop6h 20m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/24

Compare providers for flights from Montrose to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Montrose to Midway in September.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Montrose-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Montrose-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Montrose-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Montrose-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Montrose-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Montrose to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Montrose with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Montrose to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Montrose to Chicago Midway?

    For a flight from Montrose to Chicago Midway, you will be flying from Montrose County. Montrose County (MTJ) is just 2.3 mi from the center of the city. Montrose County is the only Montrose airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Montrose County on a regular basis.

  • How long is the flight from Montrose to Chicago Midway Airport?

    There are many flights that can get you from Montrose to Chicago Midway Airport in 8h 20m. Fly via Southwest to get the fastest option. The distance from Montrose to Chicago Midway Airport is about 1085 mi.

  • Can I find deals for flights from Montrose to Midway that include hotel bookings?

    Yes. In addition to deals on Montrose to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Montrose to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Montrose to Midway.

  • Can I find deals for business class flights from Montrose to Midway?

    Yes. Cheapflights offers flight deals from Montrose to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Montrose to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Montrose to Chicago Midway Airport (average of $160). Flying from Montrose to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.