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$63+ Cheap flights from Colorado 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Colorado to Midway

Keep the following information in mind while searching for Colorado to Midway flight deals. Data was last updated September 17, 2025.

Round-trip from

$116
(Priceline)

One-way from

$63
(Cheapflightsfares)

Popular in

May

Cheapest in

October

Average price

$195

Good round-trip deal

$165 or less

Good one-way deal

$118 or less
From Colorado to Chicago Midway
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One-way flight from Colorado to Chicago Midway
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Highest demand for flights based on searches. 9% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Colorado to Chicago Midway.
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Price to beat on a one-way flight from Colorado to Chicago Midway.
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Find flight deals from Colorado to Midway

Cheapest flights from Colorado to Midway
Explore the most affordable flight options available from Colorado to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2712:59 amDEN - MDW
1 stop9h 39mFrontier
Thu 10/3012:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/15$116
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/68:05 amDEN - MDW
Nonstop2h 25mFrontier
Sun 11/96:30 amMDW - DEN
1 stop26h 06mFrontier
Deal found 9/15$117
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/68:05 amDEN - MDW
Nonstop2h 25mFrontier
Mon 11/101:37 pmMDW - DEN
1 stop8h 51mFrontier
Deal found 9/17$118
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/129:12 pmDEN - MDW
Nonstop2h 24mFrontier
Fri 10/3112:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/16$119
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/148:05 amDEN - MDW
Nonstop2h 25mFrontier
Sun 11/1612:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/15$120
This Frontier deal was found by Cheapflights users on 9/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/138:05 amDEN - MDW
Nonstop2h 25mFrontier
Thu 11/131:37 pmMDW - DEN
1 stop8h 51mFrontier
Deal found 9/17$122
This Frontier deal was found by Cheapflights users on 9/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:49 amDEN - MDW
Nonstop2h 27mFrontier
Sat 10/2510:00 amMDW - DEN
1 stop9h 21mFrontier
Deal found 9/16$123
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:16 amDEN - MDW
1 stop20h 54mFrontier
Mon 11/1712:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/15$125
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/178:58 pmDEN - MDW
Nonstop2h 26mFrontier
Mon 10/206:24 pmMDW - DEN
Nonstop2h 44mFrontier
Deal found 9/15$126
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/71:42 pmDEN - MDW
1 stop7h 26mFrontier
Fri 11/1412:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/15$127
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/178:58 pmDEN - MDW
Nonstop2h 26mFrontier
Mon 11/312:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/16$128
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:49 amDEN - MDW
Nonstop2h 27mFrontier
Sun 10/266:24 pmMDW - DEN
Nonstop2h 44mFrontier
Deal found 9/15$129

Cheapflights Fare Finder

 
Customize your flight search to find flights from Colorado 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 17, 2025.
Use the filters below to find and compare flights from Colorado to Chicago Midway Airport that are best for you.

Fly from

Colorado

Fly to

Midway

Route

Depart

Return

Price

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 10/23

6:25 am-9:45 am

Nonstop2h 20m

Chicago Midway

Mon 10/27

6:25 pm-8:05 pm

Nonstop2h 40m

$157

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 10/15

4:45 pm-8:05 pm

Nonstop2h 20m

Chicago Midway

Wed 10/22

4:35 pm-6:15 pm

Nonstop2h 40m

$157

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 10/18

7:15 pm-10:35 pm

Nonstop2h 20m

Chicago Midway

Mon 10/20

9:50 pm-11:25 pm

Nonstop2h 35m

$157

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 1/17

5:30 am-9:00 am

Nonstop2h 30m

Chicago Midway

Mon 1/19

5:40 am-7:30 am

Nonstop2h 50m

$157

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 10/25

8:20 am-11:45 am

Nonstop2h 25m

Chicago Midway

Wed 10/29

4:00 pm-5:35 pm

Nonstop2h 35m

$157

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 10/18

9:30 am-4:20 pm

1 stop5h 50m

Chicago Midway

Tue 10/21

2:45 pm-4:20 pm

Nonstop2h 35m

$167

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 11/18

8:00 am-11:25 am

Nonstop2h 25m

Chicago Midway

Thu 11/20

3:20 pm-7:50 pm

1 stop5h 30m

$167

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 10/18

9:35 am-4:45 pm

1 stop6h 10m

Chicago Midway

Wed 10/22

2:45 pm-4:20 pm

Nonstop2h 35m

$167

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 11/8

9:55 am-4:45 pm

2 stops5h 50m

Chicago Midway

Tue 12/9

2:35 pm-4:15 pm

Nonstop2h 40m

$172

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 10/28

12:30 pm-9:55 pm

1 stop8h 25m

Chicago Midway

Tue 11/4

11:25 am-7:25 pm

2 stops9h 00m

$182

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 52 results
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Best time to book a flight from Colorado to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Colorado 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.

Cheapflights Insights

Everything you need to know about your flight from Colorado to Chicago Midway Airport

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

Currently, April is the cheapest month in which you can book a flight from Colorado to Chicago Midway Airport (average of $160). Flying from Colorado 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.

What is the cheapest time of day to fly from CO to MDW?

Find hourly flight availability from Colorado to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

When flying from Colorado to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

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

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

    Departing from Colorado to Chicago Midway Airport will take you 2h 20m. There are 893 mi between Colorado and Chicago Midway Airport. Generally, flights for this route are nonstop.

  • What are the most popular routes from Colorado to Chicago Midway Airport?

    The most popular flight routes from Colorado to Chicago Midway Airport are Denver Intl - Chicago Midway, Colorado Springs - Chicago Midway and Montrose County - Chicago Midway.

  • What are the cheapest flights from Colorado to Chicago Midway Airport?

    Looking for the cheapest flight from Colorado to Chicago Midway Airport? While on average our users pay $226, our data indicates the cheapest price to be $68. The most popular route (Denver Intl - Chicago Midway), is priced around $103.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Colorado 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 Colorado to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Colorado to Chicago Midway Airport (average of $160). Flying from Colorado 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

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Alternative routes for Colorado to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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John F Kennedy Intl to Midway flights
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Fort Lauderdale to O'Hare Intl flights
Boston to Midway flights
Minneapolis to Midway flights
Love Field to O'Hare Intl flights
Reagan-National to Midway flights
Hartford to O'Hare Intl flights
Tampa to O'Hare Intl flights

Top 3 airlines flying from Colorado to Midway

Discover the top 3 airlines that operate flights from Colorado to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$66Average$166FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$284FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$195Average$247FlexibilityNo cancel feeOn-time71%

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