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Cheap Flights From Denver, Colorado To Chicago, Illinois

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Airfare Details for flights from Denver to Chicago

Flight from Denver to Chicago (DEN-MDW)

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Recently Found Prices for This Route from $271

Other travelers recently found fares from Denver to Chicago ranging from $271 to $724. Use this as a guide for your search.

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Reviews for Denver to Chicago (DEN-MDW)

based on 11 reviews
Flown this route before? Write a review
    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    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!

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    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.

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    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.

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    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.

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    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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    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!

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    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.

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    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!!!!!!!!!!!!!!!

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    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

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    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.

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    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
$271 Flight from Denver to Midway (DEN-MDW) Thu, Feb 9 - Mon, Feb 20 Frontier Airlines
$298 Flight from Denver to Midway (DEN-MDW) Thu, Feb 9 - Wed, Feb 15 Frontier Airlines
$394 Flight from Denver to Midway (DEN-MDW) Fri, Feb 10 - Mon, Feb 13 Frontier Airlines
$394 Flight from Denver to Midway (DEN-MDW) Thu, Feb 9 - Sun, Feb 12 Frontier Airlines
$394 Flight from Denver to Midway (DEN-MDW) Fri, Feb 10 - Sun, Feb 12 Frontier Airlines
$394 Flight from Denver to Midway (DEN-MDW) Thu, Feb 9 - Mon, Feb 13 Frontier Airlines
$434 Flight from Denver to Midway (DEN-MDW) Thu, Feb 9 - Mon, Feb 13 Frontier Airlines
$547 Flight from Denver to Midway (DEN-MDW) Thu, Feb 9 - Tue, Feb 14 Delta Air Lines
$548 Flight from Denver to Midway (DEN-MDW) Fri, Feb 10 - Sun, Feb 12 Frontier Airlines
$724 Flight from Denver to Midway (DEN-MDW) Thu, Feb 9 - Fri, Feb 17 Delta Air Lines
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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