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$78+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — MDW
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$131
(Cheapflightsfares)

One-way from

$78
(Kiwi.com)

Popular in

May

Cheapest in

September

Average price

$221

Good round-trip deal

$158 or less

Good one-way deal

$106 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. 11% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 31, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
jue. 10/167:10 pmDEN - MDW
Nonstop2h 28mFrontier
vie. 10/174:29 pmMDW - DEN
Nonstop2h 48mFrontier
Deal found 7/29$131
This Southwest deal was found by Cheapflights users on 7/29. 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.
sáb. 9/137:25 pmDEN - MDW
Nonstop2h 25mSouthwest
mié. 9/178:50 pmMDW - DEN
Nonstop2h 35mSouthwest
Deal found 7/29$157
This Southwest deal was found by Cheapflights users on 7/30. 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.
mié. 9/1011:55 amCOS - MDW
Nonstop2h 20mSouthwest
sáb. 9/205:35 pmMDW - COS
Nonstop2h 30mSouthwest
Deal found 7/30$217
This Delta deal was found by Cheapflights users on 7/29. 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.
mié. 8/2711:11 amCOS - MDW
1 stop5h 26mDelta
sáb. 8/309:31 amMDW - COS
2 stops8h 44mDelta
Deal found 7/29$259
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/154:50 pmMTJ - MDW
1 stop4h 50mSouthwest
mié. 10/2211:10 amMDW - MTJ
1 stop5h 55mSouthwest
Deal found 7/28$316
This Southwest deal was found by Cheapflights users on 7/31. 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.
vie. 8/1512:25 pmHDN - MDW
2 stops9h 25mSouthwest
dom. 8/178:20 amMDW - HDN
1 stop4h 30mSouthwest
Deal found 7/31$424
This Delta deal was found by Cheapflights users on 7/30. 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.
vie. 9/57:16 amASE - MDW
2 stops10h 21mDelta
dom. 9/76:00 amMDW - ASE
1 stop6h 21mDelta
Deal found 7/30$483
This Delta deal was found by Cheapflights users on 7/30. 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.
sáb. 12/135:56 amGJT - MDW
2 stops11h 40mDelta
mar. 12/1610:35 amMDW - GJT
2 stops12h 55mDelta
Deal found 7/30$569
This Delta deal was found by Cheapflights users on 7/31. 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.
dom. 12/212:45 pmMTJ - MDW
1 stop6h 20mDelta
sáb. 12/276:00 amMDW - MTJ
1 stop8h 51mDelta
Deal found 7/31$1,600

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 julio 31, 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

jue. 10/16

7:10 pm-10:38 pm

Nonstop2h 28m

Chicago Midway

vie. 10/17

4:29 pm-6:17 pm

Nonstop2h 48m

$131

DenverChicago

DEN - MDW

DENMDW

Denver Intl

sáb. 9/13

8:00 am-11:25 am

Nonstop2h 25m

Chicago Midway

mar. 9/16

8:20 am-9:55 am

Nonstop2h 35m

$157

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

mié. 9/10

11:55 am-3:15 pm

Nonstop2h 20m

Chicago Midway

sáb. 9/20

5:35 pm-7:05 pm

Nonstop2h 30m

$217

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

mié. 8/27

11:11 am-5:37 pm

1 stop5h 26m

Chicago Midway

sáb. 8/30

9:31 am-5:15 pm

2 stops8h 44m

$259

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

mié. 10/15

4:50 pm-10:40 pm

1 stop4h 50m

Chicago Midway

mié. 10/22

11:10 am-4:05 pm

1 stop5h 55m

$316

HaydenChicago

HDN - MDW

HDNMDW

Hayden Yampa Valley

vie. 8/15

12:25 pm-10:50 pm

2 stops9h 25m

Chicago Midway

dom. 8/17

8:20 am-11:50 am

1 stop4h 30m

$424

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

vie. 9/5

7:16 am-6:37 pm

2 stops10h 21m

Chicago Midway

dom. 9/7

6:00 am-11:21 am

1 stop6h 21m

$483

Grand JunctionChicago

GJT - MDW

GJTMDW

Grand Junction Regnl

jue. 8/7

6:54 pm-8:44 am

2 stops12h 50m

Chicago Midway

jue. 8/14

9:15 am-6:15 pm

2 stops10h 00m

$843

DenverChicago

DEN - MDW

DENMDW

Denver Intl

vie. 9/26

12:28 pm-3:53 pm

Nonstop2h 25m

$78

DenverChicago

DEN - MDW

DENMDW

Denver Intl

mié. 9/3

2:50 pm-6:10 pm

Nonstop2h 20m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 17 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 julio 31, 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.

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 julio 31, 2025.
See what other customers who have flown with Southwest, Delta, and Allegiant Air from Colorado to Chicago Midway Airport have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

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
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

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.
Allegiant Air
7.2
Good
702 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

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.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

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 Colorado to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Colorado to Chicago Midway Airport one-way?

    $78 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Allegiant Air, with prices starting from $79 and $114, respectively.

  • 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: Southwest (61%), Frontier (46%), United Airlines( 0%).

  • 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 $185, our data indicates the cheapest price to be $49. The most popular route (Denver Intl - Chicago Midway), is priced around $154.

  • 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
Valparaiso
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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San Francisco 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$64Average$163FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$288FlexibilityNo cancel feeOn-time63%

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