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Midway

$85+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Mon 3/212:59 am
DEN
-
MDW
1 stop17h 08m
Frontier
Sat 3/72:16 pm
MDW
-
DEN
1 stop8h 23m
Frontier
Deal found 1/28$124
This Expedia deal was found by Cheapflights users on 1/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1811:25 pm
DEN
-
MDW
1 stop13h 31m
Frontier
Mon 2/236:45 am
MDW
-
DEN
1 stop15h 34m
Frontier
Deal found 1/27$138
This Trip.com deal was found by Cheapflights users on 1/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
DEN
-
MDW
1 stop6h 08m
Frontier
Mon 3/22:19 pm
MDW
-
DEN
1 stop8h 22m
Frontier
Deal found 1/27$146
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sat 3/710:20 am
DEN
-
MDW
1 stop9h 01m
Frontier
Mon 3/95:13 pm
MDW
-
DEN
1 stop7h 42m
Frontier
Deal found 1/26$147
This Frontier deal was found by Cheapflights users on 1/28. 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.
Wed 2/1812:59 am
DEN
-
MDW
1 stop9h 28m
Frontier
Mon 2/238:15 am
MDW
-
DEN
1 stop8h 06m
Frontier
Deal found 1/28$148
This CheapOair deal was found by Cheapflights users on 1/28. 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.
Wed 2/1811:59 pm
DEN
-
MDW
1 stop13h 27m
Frontier
Sat 2/216:00 am
MDW
-
DEN
1 stop7h 38m
Frontier
Deal found 1/28$149
This Expedia deal was found by Cheapflights users on 1/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/141:33 pm
DEN
-
MDW
1 stop6h 35m
Frontier
Thu 2/1912:22 pm
MDW
-
DEN
1 stop10h 19m
Frontier
Deal found 1/26$154
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Mon 2/1612:59 am
DEN
-
MDW
1 stop17h 08m
Frontier
Wed 2/187:00 am
MDW
-
DEN
1 stop15h 35m
Frontier
Deal found 1/27$156
This Trip.com deal was found by Cheapflights users on 1/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2511:25 pm
DEN
-
MDW
1 stop13h 31m
Frontier
Sat 2/286:25 am
MDW
-
DEN
1 stop7h 12m
Frontier
Deal found 1/26$157
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Mon 3/25:01 am
DEN
-
MDW
1 stop14h 26m
Frontier
Wed 3/47:15 am
MDW
-
DEN
1 stop15h 20m
Frontier
Deal found 1/27$158
This Frontier deal was found by Cheapflights users on 1/27. 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 4/236:30 am
DEN
-
MDW
1 stop7h 19m
Frontier
Tue 4/286:00 am
MDW
-
DEN
1 stop7h 09m
Frontier
Deal found 1/27$160
This Booking.com deal was found by Cheapflights users on 1/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/129:00 pm
DEN
-
MDW
1 stop23h 29m
Frontier
Thu 2/193:00 pm
MDW
-
DEN
1 stop7h 17m
Frontier
Deal found 1/27$161

Find flight deals from Colorado to Midway

Keep the following information in mind while searching for Colorado to Midway flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$124
(Kiwi.com)

One-way from

$85
(Super.com)

Popular in

November

Cheapest in

February

Average price

$212

Good round-trip deal

$236 or less

Good one-way deal

$148 or less
Provider with most accurate pricing for Denver Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Denver Intl-Chicago (CHI) flights.
Search Deals
From Colorado to Chicago Midway
Search Deals
One-way flight from Colorado to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Colorado to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Colorado to Chicago Midway.
Search Deals

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 January 29, 2026.
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

Wed 4/29

6:35 am-9:55 am

Nonstop2h 20m

Chicago Midway

Tue 5/5

10:10 am-11:50 am

Nonstop2h 40m

$185

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 4/24

5:35 pm-9:05 pm

Nonstop2h 30m

Chicago Midway

Mon 4/27

6:00 am-7:40 am

Nonstop2h 40m

$191

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Mon 4/6

7:30 pm-10:50 pm

Nonstop2h 20m

Chicago Midway

Wed 4/8

12:20 pm-5:20 pm

1 stop6h 00m

$195

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 2/26

6:15 pm-9:45 pm

Nonstop2h 30m

Chicago Midway

Mon 3/2

11:20 am-1:05 pm

Nonstop2h 45m

$195

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 2/18

10:15 am-4:25 pm

1 stop5h 10m

Chicago Midway

Sat 2/21

8:45 pm-10:30 pm

Nonstop2h 45m

$197

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 2/25

6:10 am-12:46 pm

1 stop5h 36m

Chicago Midway

Tue 3/3

12:45 pm-7:21 pm

1 stop7h 36m

$199

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 4/21

12:55 am-9:56 am

1 stop8h 01m

Chicago Midway

Thu 4/23

6:00 am-1:32 pm

1 stop8h 32m

$205

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 3/3

12:59 am-9:54 am

1 stop7h 55m

Chicago Midway

Mon 3/9

1:10 pm-5:17 pm

1 stop5h 07m

$205

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 3/5

11:10 am-5:45 pm

1 stop5h 35m

Chicago Midway

Sat 3/7

6:20 pm-8:05 pm

Nonstop2h 45m

$205

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 3/5

11:10 am-5:40 pm

1 stop5h 30m

Chicago Midway

Sun 3/8

10:05 pm-11:45 pm

Nonstop2h 40m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 60 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, February is the cheapest month in which you can book a flight from Colorado to Chicago Midway Airport (average of $60). Flying from Colorado to Chicago Midway Airport in July is currently the most expensive (average of $156). 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 January 29, 2026.

When flying from Colorado to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 47% versus a flight at noon.

What is the cheapest day to fly from Colorado to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Colorado to Midway. Price data was last updated on January 24, 2026.

Travelers seeking maximum savings on their Colorado to Chicago Midway Airport flight should consider departing on Saturday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 Grand Junction Regnl - Chicago Midway.

  • What are the most reliable airlines from Colorado to Chicago Midway Airport?

    Before booking your flight to Chicago Midway Airport from Colorado, check out the most reliable airlines to get you to your destination on time: Frontier (85%), Southwest (75%), Volaris( 70%).

  • 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 $278, our data indicates the cheapest price to be $71. The most popular route (Denver Intl - Chicago Midway), is priced around $160.

  • 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, February is the cheapest month in which you can book a flight from Colorado to Chicago Midway Airport (average of $60). Flying from Colorado to Chicago Midway Airport in July is currently the most expensive (average of $156). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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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Minneapolis to Midway flights
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Top 2 airlines flying from Colorado to Midway

Discover the top 2 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$78Average$178FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$289FlexibilityNo cancel feeOn-time63%

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