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$76+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$149
(Cheapflightsfares)

One-way from

$76
(Southwest)

Popular in

March

Cheapest in

September

Average price

$178

Good round-trip deal

$188 or less

Good one-way deal

$103 or less
Provider with most accurate pricing for Denver Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Denver Intl-Chicago (CHI) flights.
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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. 8% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Thu 5/153:42 pmDEN - MDW
Nonstop2h 26mFrontier
Tue 5/272:44 pmMDW - DEN
Nonstop2h 49mFrontier
Deal found 4/29$149
This Southwest deal was found by Cheapflights users on 4/29. 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.
Wed 6/47:25 pmDEN - MDW
Nonstop2h 25mSouthwest
Wed 6/115:15 amMDW - DEN
Nonstop2h 35mSouthwest
Deal found 4/29$151
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 6/1212:55 amDEN - MDW
1 stop6h 46mDelta
Thu 6/196:47 pmMDW - DEN
1 stop6h 34mDelta
Deal found 4/29$217
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 8/96:00 amCOS - MDW
1 stop8h 27mDelta
Wed 8/206:00 amMDW - COS
1 stop7h 50mDelta
Deal found 4/29$259
This Southwest deal was found by Cheapflights users on 4/29. 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.
Fri 7/253:50 pmCOS - MDW
Nonstop2h 25mSouthwest
Tue 7/296:55 amMDW - COS
1 stop6h 00mSouthwest
Deal found 4/29$272
This Southwest deal was found by Cheapflights users on 4/30. 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.
Fri 7/111:55 pmMTJ - MDW
2 stops10h 10mSouthwest
Sun 7/136:25 amMDW - MTJ
2 stops9h 05mSouthwest
Deal found 4/30$418
This Delta deal was found by Cheapflights users on 4/29. 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.
Tue 6/248:05 amASE - MDW
1 stop6h 36mDelta
Tue 7/16:00 amMDW - ASE
1 stop6h 22mDelta
Deal found 4/29$419
This Delta deal was found by Cheapflights users on 4/30. 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.
Fri 5/3011:10 amGJT - MDW
2 stops9h 17mDelta
Sun 6/11:55 pmMDW - GJT
2 stops9h 35mDelta
Deal found 4/30$653

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 May 1, 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 5/15

3:42 pm-7:08 pm

Nonstop2h 26m

Chicago Midway

Tue 5/27

2:44 pm-4:33 pm

Nonstop2h 49m

$149

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 6/4

5:55 am-9:20 am

Nonstop2h 25m

Chicago Midway

Wed 6/4

4:35 pm-6:20 pm

Nonstop2h 45m

$151

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 6/12

12:55 am-8:41 am

1 stop6h 46m

Chicago Midway

Fri 6/20

6:47 pm-12:21 am

1 stop6h 34m

$217

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 8/9

6:00 am-3:27 pm

1 stop8h 27m

Chicago Midway

Wed 8/20

6:00 am-12:50 pm

1 stop7h 50m

$259

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 7/25

3:50 pm-7:15 pm

Nonstop2h 25m

Chicago Midway

Tue 7/29

6:55 am-11:55 am

1 stop6h 00m

$272

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Fri 7/11

1:55 pm-1:05 am

2 stops10h 10m

Chicago Midway

Sun 7/13

6:25 am-2:30 pm

2 stops9h 05m

$418

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Tue 6/24

8:05 am-3:41 pm

1 stop6h 36m

Chicago Midway

Tue 7/1

6:00 am-11:22 am

1 stop6h 22m

$419

Grand JunctionChicago

GJT - MDW

GJTMDW

Grand Junction Regnl

Fri 5/30

11:10 am-9:27 pm

2 stops9h 17m

Chicago Midway

Sun 6/1

1:55 pm-10:30 pm

2 stops9h 35m

$653

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 7/5

5:00 am-8:25 am

Nonstop2h 25m

$76

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 5/15

3:42 pm-7:08 pm

Nonstop2h 26m

$96

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 19 results
1
2

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 May 1, 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Frontier from Colorado to Chicago by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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?

    $76 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Frontier and Delta, with prices starting from $97 and $109, 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 Aspen Pitkin 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 $210, our data indicates the cheapest price to be $75. The most popular route (Denver Intl - Chicago Midway), is priced around $104.

  • 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 Colorado?

Book flights to Colorado if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$144FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$163Average$292FlexibilityNo cancel feeOn-time63%

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