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$180+ 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
MTJ — MDW
Mar 20 — Mar 271
Fri 3/20
Fri 3/27
1 adult, Economy
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Cheap 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 February 18, 2026.

This Southwest deal was found by Cheapflights users on 2/17. 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 4/108:25 am
MTJ
-
MDW
1 stop4h 55m
Southwest
Tue 4/141:55 pm
MDW
-
MTJ
2 stops7h 00m
Southwest
Deal found 2/17$379
This Southwest deal was found by Cheapflights users on 2/14. 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 3/141:40 pm
MTJ
-
MDW
1 stop10h 10m
Southwest
Fri 3/203:00 pm
MDW
-
MTJ
1 stop5h 45m
Southwest
Deal found 2/14$388
This Southwest deal was found by Cheapflights users on 2/14. 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.
Thu 4/238:25 am
MTJ
-
MDW
1 stop4h 55m
Southwest
Sat 4/251:55 pm
MDW
-
MTJ
1 stop5h 55m
Southwest
Deal found 2/14$413
This Delta deal was found by Cheapflights users on 2/17. 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.
Wed 3/42:13 pm
MTJ
-
MDW
1 stop7h 18m
Delta
Sun 3/86:00 am
MDW
-
MTJ
1 stop7h 49m
Delta
Deal found 2/17$419
This Southwest deal was found by Cheapflights users on 2/15. 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 5/88:25 am
MTJ
-
MDW
1 stop4h 55m
Southwest
Tue 5/1212:35 pm
MDW
-
MTJ
1 stop8h 20m
Southwest
Deal found 2/15$432
This Southwest deal was found by Cheapflights users on 2/17. 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 6/88:00 am
MTJ
-
MDW
1 stop7h 20m
Southwest
Wed 6/102:45 pm
MDW
-
MTJ
1 stop5h 40m
Southwest
Deal found 2/17$434

Find 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 February 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$379
(Southwest)

One-way from

$180
(Southwest)

Popular in

November

Cheapest in

February

Average price

$239
Provider with most accurate pricing for Montrose County-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montrose County-Chicago (CHI) 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. 27% potential increase in price ($167 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 18, 2026.
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 4/10

8:25 am-2:20 pm

1 stop4h 55m

Chicago Midway

Tue 4/14

1:55 pm-7:55 pm

2 stops7h 00m

$379

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Fri 4/17

8:25 am-2:20 pm

1 stop4h 55m

Chicago Midway

Mon 4/20

11:40 am-7:10 pm

1 stop8h 30m

$379

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Thu 5/7

8:25 am-2:20 pm

1 stop4h 55m

Chicago Midway

Mon 5/11

3:30 pm-7:10 pm

1 stop4h 40m

$413

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Thu 4/23

8:25 am-2:20 pm

1 stop4h 55m

Chicago Midway

Sat 4/25

9:15 am-6:50 pm

2 stops10h 35m

$418

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Wed 3/4

2:13 pm-10:31 pm

1 stop7h 18m

Chicago Midway

Sun 3/8

6:00 am-12:49 pm

1 stop7h 49m

$419

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Fri 5/8

8:25 am-2:20 pm

1 stop4h 55m

Chicago Midway

Tue 5/12

12:35 pm-7:55 pm

1 stop8h 20m

$432

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Tue 3/24

12:35 pm-7:45 pm

2 stops6h 10m

$180

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Fri 2/27

2:13 pm-10:31 pm

1 stop7h 18m

$429

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/17

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 4h 55m. 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.

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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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