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Cheap Flights From Denver, Colorado (DEN) To Chicago, Illinois (MDW)

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Fares from Denver, CO (DEN)
$145 RT to
Chicago, IL (MDW)
Sorry this deal is over or has been sold out! But here’s another great Airfarewatchdog verified fare for this route!
$145 RT Denver to Chicago, IL
Airline(s)
Frontier
Seats:
Seats are not available on all flights or all dates of travel. You may need to have flexible travel dates to find this fare. Fares for travel on holidays may be higher.
Adv. Purchase:
9 Days
Available:
Tue-Sat
Travel Starting:
Friday, 07 November 2014
More Details:
Lowest fare found for travel within the next 30 days.
Last Updated:
Thursday, 30 October 2014
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All mandatory taxes/fees are included in the price. Tax-inclusive fare may be a few dollars higher or lower depending on the airport you connect through, if any. Baggage fees, if applicable, and other optional fees are not included.

Our Dealhounds found this airfare using flexible date search. This means we searched a range of dates to find you the best price.

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More Flights From Denver To Chicago (DEN-MDW)

Price
Details
$258 RT Non-Stop Flights. No min. stay. Fare can be bought one-way for half the... (Southwest) See all details »
  • Airline(s):
    Southwest
  • Seats are:
    Seats Are Not Available On All Flights Or All Dates Of Travel. You May Need To Have Flexible Travel Dates To Find This Fare. Fares For Travel On Holidays May Be Higher.
  • Available for travel:
    Mon-Thur & Sat
  • Travel starting:
    Wednesday, 03 December 2014
  • Travel ending:
    Wednesday, February 11, 2015
  • More Details:
    Non-Stop Flights, No Min. Stay, Fare Can Be Bought One-way For Half The Lowest Roundtrip Price, No Peak Holiday Travel At This Price
  • Last Updated:
    Thursday, October 30, 2014
  • Our Notes:
    This is a fare from Southwest - visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find the best ...moreoption.

Reviews for Denver to Chicago (DEN-MDW)

based on 13 reviews
Flown this route before? Write a review
    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Love Southwest, Sorry Frontier...

    by juderulz on November 28, 2013

    Flight from Denver to Chicago

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    October 2013
    Seat Class:
    economy

    As a Colorado native, I have grown up loving Frontier and always flying them ~ Unfortunately since the company has changed hands, the baggage fees and higher ticket prices just don't make it worth it. This and I have ALWAYS had great service with Southwest! Thanks for coming to Denver!

    1. Flight Rating

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    4. Seat Comfort:

    Disaster on Return Flight

    by LostSpirit on November 12, 2012

    Flight from Denver to Chicago

    Airline:
    Spirit Airlines
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    May 2012
    Seat Class:
    economy

    Was so excited when Spirit started flying to Denver. Was on their first flight to Denver from Chicago. Was uneventful. Knew about no food or drink and baggage fees prior to flight.

    The return flight to Chicago was a total disaster. Supposedly the aircraft had to have a tire changed, so they told us!!! Told 1 hr delay. Then we were told that the part had to be flown in and now we had another 3 hour delay. When asked about booking on other airlines, they said we would have to do it on our own and no compensation from Spirit. They told us lie after lie about departure time. We finally departed at 2 AM, more than 12 hours from our original departure time!! When I called the operations manager the next day to complain, he was upset that I had his phone number; then he proceeded to inform me that there would be a $50 voucher online in my account. Had to be redeemed on another Spirit flight within 60 days!!! Was never notified via e-mail about the voucher, nor ever received any kind of apology. Needless to say, I never used the voucher and will never fly Spirit again. They are uncaring and disrespectful of their customers....

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    Bags Fly free.....

    by Jeffro641 on December 30, 2010

    Flight from Denver to Chicago

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    1 stop in Kansas City, Missouri
    Date of Flight:
    December 2010
    Seat Class:
    economy

    Coming home from Christmas with gifts and the extra 5 pounds over cost me $50.00. I think i was working with a Grinch as she would not let it slide at all. I hope she got coal for me beeing out another 50 bucks during the holiday. Bah Hum bug indeed!

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Either TSA or Frontier broke my lock

    by mrtime on November 5, 2010

    Flight from Denver to Chicago

    Airline:
    Frontier
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    October 2010
    Seat Class:
    economy

    When I claimed my bag in Chicago, I noticed the lock on the zipper had been broken and the zipper itself was damaged beyond repair - my return trip was either going to require a new suitcase or i would just have to trust that my belongings would be safe without a lock.

    I spoke to the Frontier baggage representative who said it was not Frontier's fault and that, once the bag is out of their hands, it's TSA's responsibility.

    Since TSA answers to nobody, I have no recourse. This is the second time I have had a bag damaged this year. Both flights were with Frontier and both times Frontier passed the buck to TSA.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Smooth trip - no problems

    by grandmasharyn on October 28, 2010

    Flight from Denver to Chicago

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    October 2010
    Seat Class:
    economy

    as always, as expected Southwest competes with the best, always enjoy the flights- no surprises. Smooth take off, and smooth landing.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Very entertaining!

    by torresdebbie60 on October 21, 2010

    Flight from Denver to Chicago

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    October 2010
    Seat Class:
    economy

    We had a steward who made the safety lecture entertaining. He had a joke for each step of the procedure....example....he said, "In case this flight becomes a cruise, you will use your seat as a floating device." He had the whole plane cracking up, and when he was through we gave him a round of applause.

    1. Flight Rating

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    3. In-flight Service:

    4. Seat Comfort:

    We prefer to fly Frontier

    by Zachster on October 8, 2010

    Flight from Denver to Chicago

    Airline:
    Frontier
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    October 2010
    Seat Class:
    economy

    Smooth flight - on time - pleasant, helpful crew. Seating was somehow more comfortable than some other carriers, even without their additional stretch seating.

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    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    The only way to travel

    by beans1957 on September 16, 2010

    Flight from Denver to Chicago

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    September 2010
    Seat Class:
    economy

    Southwest was very efficient from start to finish and the no charge for bags cinches the deal!Flight attendants were friendly and service was great!

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Everything was so easy!

    by Skibunny on August 29, 2010

    Flight from Denver to Chicago

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    August 2010
    Seat Class:
    economy

    I needed to extend our trip after I booked it and It was so easy to make the change online. When I called a representative to make sure I was doing it correctly, she said although she couldn't book the webfare special rates, only the regular rates, she would stay on the line and walk me through it. Southwest does not charge for any of the above services.

    We checked bags, again at no charge. We loved the open seating and the process for lining up at numbered poles to board. Everyone sat quickly and we left on time. We liked that there were no beverage carts but the attendants took orders by hand and we were served quickly. Everything was just easy and relaxed.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Love that they don't charge for luggage nor to change your flight!

    by jhardy15 on August 12, 2010

    Flight from Denver to Chicago

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    July 2010
    Seat Class:
    economy

    Southwest is awesome! The only airline not charging for luggage and their flight prices are the same if not lower than the rest of the airlines (so they aren't making it up in increased flight prices).

    And if I can't make my flight and I let them know outside of 24 hours, I get my unused flight as credit to be used at another time...no charge! Or if I need to change my flight all i pay is the price difference or they refund me if the flight is cheaper than what i originally payed. Love Southwest!!!!!!!!!!!!!!!

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    terrible

    by rogerpos on July 16, 2010

    Flight from Denver to Chicago

    Airline:
    Midwest Airlines
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    June 2010
    Seat Class:
    economy

    On the outbound flight the airlines over booked the flight and we got the worst seats and were seperated even though we had reservations 3 months prior to the flight.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Love Southwest

    by dustin on July 16, 2010

    Flight from Denver to Chicago

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    June 2010
    Seat Class:
    economy

    I believe when you go on vacation you bring luggage and I am not about to pay for it so Southwest is the only airline I will fly...and it is the best experience I have had on a plane in years. Being from Colorado I used to fly Frontier to support my home town business but sorry you got greedy charging for luggage so no more.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Frontier rocks

    by kazakhmom on July 5, 2010

    Flight from Denver to Chicago

    Airline:
    Frontier
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    June 2010
    Seat Class:
    economy

    Love Frontier! The staff are always courteous, the plane clean, and in-flight satellite tv/movies (extra fee) a nice plus. I'm a larger person and their seats are quite comfy. Travel in/out of Midway is so much easier than O'Hare.

Flown this route before? Write a review
Sample Fares found by other travelers within the past 72 hours
Price From/To Depart/Return Airline
$462 Flight from Denver to Midway (DEN-MDW) Thu, Jun 5 - Sat, Jun 7 Delta Air Lines
$478 Flight from Denver to Midway (DEN-MDW) Fri, Jun 6 - Fri, Jun 13 Frontier Airlines
$478 Flight from Denver to Midway (DEN-MDW) Sat, Jun 7 - Tue, Jun 10 Frontier Airlines
$478 Flight from Denver to Midway (DEN-MDW) Sat, Jun 7 - Wed, Jun 11 Frontier Airlines
$478 Flight from Denver to Midway (DEN-MDW) Fri, Jun 6 - Mon, Jun 9 Frontier Airlines
$478 Flight from Denver to Midway (DEN-MDW) Fri, Jun 6 - Sun, Jun 8 Frontier Airlines
$478 Flight from Denver to Midway (DEN-MDW) Thu, Jun 5 - Sun, Jun 8 Frontier Airlines
$498 Flight from Denver to Midway (DEN-MDW) Sun, Jun 8 - Mon, Jun 9 Frontier Airlines
$498 Flight from Denver to Midway (DEN-MDW) Thu, Jun 5 - Sun, Jun 8 Frontier Airlines
$498 Flight from Denver to Midway (DEN-MDW) Thu, Jun 5 - Wed, Jun 11 Frontier Airlines
There are approximately 51 flights covering the route from Denver International Airport in Denver to Midway Airport in Chicago, provided by as many as 6 airlines.

The following airlines sometimes offer nonstop cheap flights from Denver to Chicago:

Transwest Air

As an alternative to flying from Denver, you may also want to try searching for cheap flights from Colorado Springs (COS).
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