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DEN - MDW

$29 Find cheap flights from Denver to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Denver to Midway departing on 6/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/22
Sat 6/29

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Denver to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Denver to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,800,826 times on KAYAK, and here is why:

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Cheap flight deals from Denver to Midway (DEN-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Denver to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
1:46 pm - 5:12 pmDEN-MDW
2h 26mnonstop
6:00 am - 7:44 amMDW-DEN
2h 44mnonstop
$58Frontier
Find Deal
Tue, Jun 4 - Tue, Jun 11
7:44 am - 11:09 amDEN-MDW
2h 25mnonstop
6:00 am - 7:47 amMDW-DEN
2h 47mnonstop
$60Frontier
Find Deal
Wed, May 29 - Tue, Jun 4
8:38 am - 12:00 pmDEN-MDW
2h 22mnonstop
10:26 pm - 12:20 amMDW-DEN
2h 54mnonstop
$67Frontier
Find Deal
Wed, Jun 12 - Sat, Jun 15
7:44 am - 11:09 amDEN-MDW
2h 25mnonstop
6:15 am - 7:56 amMDW-DEN
2h 41mnonstop
$68Frontier
Find Deal
Wed, May 29 - Wed, Jul 24
8:25 am - 11:47 amDEN-MDW
2h 22mnonstop
10:26 pm - 12:20 amMDW-DEN
2h 54mnonstop
$70Frontier
Find Deal
Sat, Jun 15 - Sat, Jun 22
7:48 am - 11:13 amDEN-MDW
2h 25mnonstop
10:01 pm - 11:58 pmMDW-DEN
2h 57mnonstop
$71Frontier
Find Deal
Sat, Jun 1 - Sat, Jun 1
1:46 pm - 5:10 pmDEN-MDW
2h 24mnonstop
2:06 pm - 3:51 pmMDW-DEN
2h 45mnonstop
$72Frontier
Find Deal
Tue, Jun 18 - Tue, Jun 25
6:19 pm - 9:45 pmDEN-MDW
2h 26mnonstop
10:26 pm - 12:20 amMDW-DEN
2h 54mnonstop
$77Frontier
Find Deal
Thu, Jun 13 - Sat, Jun 15
7:44 am - 11:09 amDEN-MDW
2h 25mnonstop
5:55 am - 7:41 amMDW-DEN
2h 46mnonstop
$78Frontier
Find Deal
Mon, Jun 3 - Wed, Jun 5
12:59 am - 8:51 amDEN-MDW
6h 52m1 stop
9:46 am - 2:05 pmMDW-DEN
5h 19m1 stop
$233Delta
Find Deal
Fri, May 31 - Tue, Jun 4

Flights from Denver to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Denver to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Denver to Chicago Midway Airport?

The average price of all flights from Denver to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago Midway Airport on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Denver to Chicago Midway Airport. For your return ticket, we recommend flying on a Tuesday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Denver to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Denver to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Denver to Chicago Midway Airport is January, where tickets cost $88 on average. On the other hand, the most expensive months are December and July, where the average cost of tickets is $218 and $205 respectively.

How far in advance should I book a flight from Denver to Chicago Midway Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Denver to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Denver to Chicago Midway Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 63 days before departure.

Which airlines provide the cheapest flights from Denver to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, Frontier offered the best one-way deal for that route, at $29. KAYAK users also found Denver to Chicago Midway Airport round-trip flights on Frontier from $58 and on Delta from $233.

Which airlines fly non-stop between Denver and Chicago Midway Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Denver to Chicago Midway Airport.
There are 2 airlines that fly nonstop from Denver to Chicago Midway Airport. They are Frontier and Southwest. The cheapest airline for this route is Frontier, with the best one-way deal found costing $58. On average, the best prices for this route can be found at Frontier.

How many flights are there between Denver and Chicago Midway Airport per day?

Each day, there are between 13 and 23 nonstop flights that take off from Denver and land in Chicago Midway Airport, with an average flight time of 2h 20m. The most common departure time is 7:00 am and most flights take off in the morning. Each week, there are 128 flights. The most frequent day of departure is Thursday, when 18% of all weekly flights depart. The fewest flights depart on a Wednesday.

Which cabin class options are there for flights between Denver and Chicago Midway Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Denver to Chicago Midway Airport take?

The duration of a nonstop flight to Chicago Midway Airport from Denver is typically 2h 22m. The journey crosses a distance of 893 miles.

What’s the earliest departure time from Denver to Chicago Midway Airport?

Early birds can take the earliest flight from Denver at 5:10 am and will be landing in Chicago Midway Airport at 8:30 am.

What’s the latest departure time from Denver to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Denver to Chicago Midway Airport jets off at 9:55 pm and lands at 1:15 am.

Good to know

Low season

February

High season

November

Cheapest flight

$29
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Denver to Chicago Midway Airport

When to book flights from Denver to Midway

Are your dates flexible? Find out the best times to travel from Denver to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Denver to Chicago Midway Airport flights

  • What seat selection options are available on Southwest flights from Denver to Chicago Midway Airport?

    On Southwest Airlines flights from Denver to Chicago Midway Airport, seat selection options are based on the airline's open seating policy, also known as “Aisle or Window” seating. Unlike other airlines, Southwest does not assign specific seats to passengers. Instead, passengers are assigned a boarding group (A, B, or C), and within each group, a boarding position number (1-60).

  • What services does Delta offer economy passengers on flights from Denver to Chicago Midway Airport?

    Delta provides personal seat-back screens to every passenger where they can access a wide selection of movies, TV shows, music, and games. The airline offers Wi-Fi connectivity on flights from Denver to Chicago Midway Airport for a fee, and passengers can choose from different packages depending on their need for connections.

  • What is the luggage allowance on Frontier flights from Denver to Chicago Midway Airport?

    Frontier Airlines is a budget airline that charges for most services, including checked baggage. The luggage allowance varies depending on the type of fare purchased by the passenger. Passengers who pick Basic Economy fare on Frontier flights from Denver to Chicago Midway Airport are only entitled to one small personal item. Passengers who pick Standard Economy fare can bring one personal item and one carry-on bag. The carry-on bag's maximum dimensions must be 24 × 16 × 10 inches, and it should fit in the overhead bin.

  • How do I get from Chicago Midway Airport (MDW) to the city center?

    You can take the CTA Orange Line train from Midway Airport to Downtown Chicago. The train runs every few minutes and takes about 25–30 minutes to reach the city center. Additionally, several airport shuttle companies operate at Midway Airport, offering shared or private shuttle services to the city center. The fares vary depending on the company and the type of service.

  • What is the cheapest flight from Denver to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Denver to Chicago Midway Airport was $29 for a one-way ticket and $58 for a round-trip.

  • Do I need a passport to fly between Denver and Chicago Midway Airport?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Denver to Chicago Midway Airport?

    Denver airport is called Denver Intl and the only airport in Chicago Midway Airport is Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Denver to Chicago Midway Airport?

    American Airlines, Delta, and JetBlue offer inflight Wi-Fi service on the Denver to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Denver to Chicago Midway Airport?

    The Airbus A320neo is the aircraft model that flies most regularly on the Denver to Chicago Midway Airport flight route.

  • On which days can I fly direct from Denver to Chicago Midway Airport?

    There are nonstop flights from Denver to Chicago Midway Airport on a daily basis.

  • Which is the best airline for flights from Denver to Chicago, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Denver to Chicago are Delta and Frontier. With an average price for the route of $474 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $139 and an overall rating of 6.2.

  • How does KAYAK find such low prices on flights from Denver to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Denver to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Denver to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Denver is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Denver to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Denver with another airline. Booking your flights between Denver and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Denver to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Denver up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Denver to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $47 or less one-way and $82 or less round-trip.
  • Delta Air Lines offers flights from Denver to Chicago Midway Airport and has taken several steps to reduce carbon emissions and promote sustainability. The airline has committed to using 10% SAF by 2030. SAF is made from sustainable materials, such as waste oil, and it can reduce CO2 emissions by up to 80% compared to traditional jet fuel.
  • Chicago Midway Airport (MDW) serves various nearby cities including Bedford Park, Burbank, Bridgeview, Evergreen Park, Oak Lawn, Chicago Ridge, Alsip, Worth, Palos Hills, and Crestwood. These locations are all accessible by car from the airport.
  • Spirit Airlines provides wheelchair assistance on flights from Denver to Chicago Midway Airport from check-in to boarding and then upon arrival at the destination. Passengers can request a wheelchair at the airport or during the booking process. Airport staff will assist passengers with mobility issues in navigating through the airport terminals.
  • Denver International Airport (DEN) has three main passenger terminals. The Jeppesen Terminal is the Main Terminal, and it serves airlines such as Delta, and United Airlines, which offer flights from Denver to Chicago Midway Airport.
  • Frontier Airlines welcomes pets on board their flights from Denver to Chicago Midway Airport. They accept small cats and dogs as carry-on baggage in the aircraft cabin, and larger pets as checked baggage in the cargo hold. There is a fee for bringing a pet as a carry-on.
See more tips

Prefer to fly non-stop from Denver to Chicago Midway Airport?

Find which airlines fly direct from Denver Intl to Midway, which days they fly and book direct flights.

Nonstop departures

Denver Intl to Chicago Midway

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Frontier, Southwest

Frontier, Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights

Nonstop returns

Chicago Midway to Denver Intl

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Frontier, Southwest

Frontier, Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights
See more direct flights

Top 3 airlines serving from Denver to Midway

 
See real verified KAYAK customer reviews for airlines flying from Denver to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Denver to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10561 reviews
8.0Entertainment
8.2Boarding
7.9Comfort
8.6Crew
7.4Food
Airline reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

6.0 GoodPeter, May 2024SLC - HNL
Read more about Delta reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Generally good but there wasn’t any staff available when my luggage didn’t appear at baggage claim in Fresno. It took about half an hour to locate a staff member to open up the locked room where it was being kept.

Flight delayed from Cape Town to Washington then got diverted to miami and in miami we had to fend for ourselves , im still trying to get to Shreveport now

I just wrote a text which was supposed to be for the flight from Denver to spokane not Frankfurt to Denver.

Too many fees (but that seems to apply to all airlines nowadays)

Flight was on time. Staff were friendly. I paid for Economy Plus but was required to check my standard carry-on luggage due to lack of space on the aircraft. This cost me 30 minutes, unexpectedly, in waiting at the baggage claim. This experience did not meet my expectations.

Everything was very good. Boarding and takeoff were on time and organized. Had a good flight

Wheelchair assistance was not complete. The person left me at the departure gate without informing the groundstaff of my requirements. I had to walk to the departure counter to ask for help to reach the plane door. The crew informed me that in future they were not allowed to help passengers like me, senior citizen and Wheelchair passenger with placing their carry on bags in the overhead compartments!

Flight was delayed by over an hour and gate checked bags took 15 minutes to be delivered to the jet bridge.

Seats are way too snug for my hip to knee ratio and the recline on the seat in front of me made my experience worst. My legs had no room at all. Not a plane for people 6 ft or over unless you fly first class.

Delayed for maintenance issue?? Should have been addressed before boarding. Put my bag on an earlier flight, but didn’t ask if I wanted to change to an earlier flight. Arrived to find my bag locked up and no agent to be found when I landed.

Fecal matter in seat back pocket. Presumably from a kids diaper.

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Left Denver late, then sat on tarmac 30 min after arrival

Everything was good, 20/30 minutes late waiting on a crew member. It’s hard to keep employees. Or serious employees I know. I remember one flight from Houston of Frontiers was almost 18 hours late. And another 4 hours late very poor. But I would rather be late and safe than the on the news. Thank you.

Bought seats on the flight and they were supposed to be 2 and a jumpseat. Plane clearly changed and it was a regular 3 seat row. Asked for a refund and was denied. If I wanted to sit next to someone else I wouldn't have bought the seats..

Lost baggage on my connecting flight. 24 hours later, still no update on my bags.

It’s a cheap airline and I wish if they had better seats.

Seats are cramped and uncomfortable. You have to pay for everything and it is very expensive.

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

Book cheap flights from Denver to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Denver to Chicago found on KAYAK in the last 72 hours.
6/4Tue
nonstopFrontier
2h 26mDEN-MDW
$29
5/29Wed
nonstopFrontier
2h 25mDEN-MDW
$30
8/27Tue
nonstopFrontier
2h 22mDEN-MDW
$37
8/20Tue
1 stopDelta
6h 49mDEN-MDW
$98
6/5Wed
1 stopDelta
6h 17mDEN-MDW
$118
6/2Sun
2 stops
24h 33mDEN-MDW
$161
6/2Sun
2 stops
24h 33mDEN-MDW
$172
6/9Sun
2 stopsAllegiant Air
26h 17mDEN-MDW
$197
8/4Sun
2 stopsAllegiant Air
26h 20mDEN-MDW
$210
6/2Sun
3 stopsSun Country Air
21h 56mDEN-MDW
$313

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Last minute flights from Denver to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Denver to Chicago that are departing in the next 10 days.
5/28Tue
nonstopFrontier
2h 26mDEN-MDW
6/11Tue
nonstopFrontier
2h 44mMDW-DEN
$107
5/28Tue
nonstopFrontier
2h 26mDEN-MDW
5/29Wed
nonstopFrontier
2h 48mMDW-DEN
$112
5/28Tue
multi-stopFrontier
17h 28mDEN-MDW
6/11Tue
nonstopFrontier
2h 44mMDW-DEN
$162
5/28Tue
nonstopFrontier
2h 26mDEN-MDW
6/3Mon
nonstopFrontier
2h 48mMDW-DEN
$177
5/26Sun
nonstopFrontier
2h 25mDEN-MDW
6/1Sat
nonstopFrontier
2h 48mMDW-DEN
$180
5/26Sun
nonstopFrontier
2h 25mDEN-MDW
5/29Wed
nonstopFrontier
2h 48mMDW-DEN
$181
5/28Tue
nonstopFrontier
2h 26mDEN-MDW
5/30Thu
nonstopFrontier
2h 57mMDW-DEN
$182
5/26Sun
nonstopFrontier
2h 27mDEN-MDW
6/1Sat
nonstopFrontier
2h 48mMDW-DEN
$185
5/28Tue
multi-stopDelta
6h 25mDEN-MDW
5/29Wed
multi-stopDelta
6h 59mMDW-DEN
$258
5/28Tue
multi-stopDelta
6h 25mDEN-MDW
5/30Thu
multi-stopDelta
9h 04mMDW-DEN
$277

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Denver - Chicago Midway Airport Flights

Departure:

Denver (DEN)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Denver

Cabin classes:

$57