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Midway

$324+ Cheap flights from Montrose (MTJ) to Midway (MDW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
MTJ — MDW
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
1 adult, Economy
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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 August 11, 2025.

Round-trip from

$324
(Southwest)

Popular in

December

Cheapest in

January

Average price

$338
From Montrose County to Chicago Midway
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
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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 August 11, 2025.

This Southwest deal was found by Cheapflights users on 8/10. 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 10/31:45 pmMTJ - MDW
1 stop6h 05mSouthwest
Mon 10/69:20 amMDW - MTJ
1 stop4h 40mSouthwest
Deal found 8/10$324
This Southwest deal was found by Cheapflights users on 8/9. 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.
Mon 11/2411:50 amMTJ - MDW
1 stop7h 20mSouthwest
Fri 11/285:15 amMDW - MTJ
1 stop6h 50mSouthwest
Deal found 8/9$409
This Delta deal was found by Cheapflights users on 8/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/212:45 pmMTJ - MDW
1 stop6h 20mDelta
Sat 12/276:00 amMDW - MTJ
1 stop8h 51mDelta
Deal found 8/9$1,560

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 August 11, 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

Fri 10/3

1:45 pm-8:50 pm

1 stop6h 05m

Chicago Midway

Mon 10/6

9:20 am-1:00 pm

1 stop4h 40m

$324

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Mon 11/24

11:50 am-8:10 pm

1 stop7h 20m

Chicago Midway

Fri 11/28

5:15 am-11:05 am

1 stop6h 50m

$409

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Sun 12/21

2:45 pm-10:05 pm

1 stop6h 20m

Chicago Midway

Sat 12/27

6:00 am-1:51 pm

1 stop8h 51m

$1,560

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/10

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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated August 11, 2025.
Read through reviews of airlines operating flights from Montrose to Chicago Midway Airport, such as Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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
Valparaiso
Chesterton

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