$107 Find Cheap Flights from Denver to Chicago Midway Airport - Compare and Save

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).

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.

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.

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.

Among airlines operating Denver to Chicago Midway Airport flights:

• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Only Southwest operates flights between Denver and Chicago Midway Airport.

Flights from Denver to Chicago Midway Airport usually depart from Denver Intl (DEN) and arrive at Chicago Midway (MDW).

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag and a checked bag in Economy Class
• JetBlue: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Two cabin classes are available on flights from Denver to Chicago Midway Airport:

• Economy Class
• Business Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $168 round-trip via Dallas/Fort Worth (DFW), compared to $282 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest. Other aircraft seen on the route include Airbus A321neo variants.

One-stop flights from Denver to Chicago Midway Airport most commonly connect through:

• Atlanta Hartsfield-Jackson (ATL) - 50% of one-stop connections
• Minneapolis St Paul (MSP) - 25% of one-stop connections
• Dallas/Fort Worth (DFW) - 17% of one-stop connections
• Detroit Metropolitan Wayne County (DTW) - 8% of one-stop connections

Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 29% on the Denver to Chicago Midway Airport route. Friday is the cheapest departure day at $247 round-trip on average, while Sunday is the most expensive at $345, a difference of $98. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Morning is the busiest departure period on Denver to Chicago Midway Airport flights, with 34% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 33%, and night flights for 0%.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

These are the earliest and latest flight times available from Denver to Chicago Midway Airport:

• Earliest: departs at 5:00 am and lands at 7:21 am
• Latest: departs at 9:10 pm and lands at 11:31 pm.

The flight takes about 2h 21m.

Last-minute fares on this route - booked within 2 weeks of departure - run 39% above the route average of $276. Book 6 weeks before departure for the lowest fares.

A nonstop flight from Denver to Chicago Midway Airport takes 2h 21m, covering 893 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $190 to $1,756. That means the highest observed fare was about 9x higher than the lowest one.

One-way fares from Denver to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $115, which is 39% below the typical average for this route.

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 6h 03m, compared with 6h 10m via Minneapolis St Paul (MSP) and 8h 48m via Atlanta Hartsfield-Jackson (ATL).

Chicago Midway Airport is 1 hour ahead of Denver (Central Time vs Mountain Time). Plan for the time shift when scheduling connections or first-day activities.

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Round-trip flights from Denver to Chicago Midway Airport range from $203 to $377, with an average of $276 over the past 12 months. Anything below $203 counts as a good deal.

JetBlue is the only airline on the Denver to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.