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Flights from Denver to Chicago – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

DEN to MDW flights and routes map DEN to MDW – All flight route options from Denver International, Colorado, USA to Chicago Midway International, Illinois, USA. These routes are operated by 4 airlines. Fly non-stop with Southwest Airlines or Frontier Airlines, or choose from 19 different stopover flights. The shortest flight time is 2 hours and 20 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
USA DEN Denver Denver, CO, USA
USA MDW Chicago Midway , IL, USA
DEN
Denver
USADenver, CO, USA
Chicago Midway
USAChicago, IL, USA
MDW
2 direct routes found »
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22 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 7-10 flights per day.

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2h 20m

Southwest Airlines
Non-stop with Southwest Airlines.
2h 20m
7-10 flights per day.
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Frontier Airlines
Non-stop with Frontier Airlines. 0-1 flights per day.

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2h 27m

Frontier Airlines
Non-stop with Frontier Airlines.
2h 27m
0-1 flights per day.
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1 stop route options with the same airline:

Duration

Via Indianapolis IND
1 stop with Southwest Airlines.
Begins in 7/8

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4h 48m

Begins in 7/8
Via Indianapolis IND
1 stop with Southwest Airlines.
4h 48m
Begins in 7/8
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Via Memphis MEM
1 stop with Southwest Airlines.
Begins in 7/10

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4h 55m

Begins in 7/10
Via Memphis MEM
1 stop with Southwest Airlines.
4h 55m
Begins in 7/10
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Via Cleveland CLE
1 stop with Southwest Airlines. 0-1 flights per day.

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4h 55m

Via Cleveland CLE
1 stop with Southwest Airlines.
4h 55m
0-1 flights per day.
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Via Kansas City MCI
1 stop with Southwest Airlines. 2-4 flights per day.

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4h 55m

Via Kansas City MCI
1 stop with Southwest Airlines.
4h 55m
2-4 flights per day.
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Via Minneapolis MSP
1 stop with Southwest Airlines. 1-3 flights per day.

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4h 55m

Via Minneapolis MSP
1 stop with Southwest Airlines.
4h 55m
1-3 flights per day.
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Via Colorado Springs COS
1 stop with Southwest Airlines. 0-1 flights per day.
Only saturdays

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5h 05m

Only saturdays
Via Colorado Springs COS
1 stop with Southwest Airlines.
5h 05m
0-1 flights per day.
Only saturdays
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Via Saint Louis STL
1 stop with Southwest Airlines. 1-6 flights per day.

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5h 10m

Via Saint Louis STL
1 stop with Southwest Airlines.
5h 10m
1-6 flights per day.
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Via Omaha OMA
1 stop with Southwest Airlines. 1-3 flights per day.

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5h 20m

Via Omaha OMA
1 stop with Southwest Airlines.
5h 20m
1-3 flights per day.
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Via Detroit DTW
1 stop with Southwest Airlines. 0-1 flights per day.
Tue & Wed

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5h 23m

Tue & Wed
Via Detroit DTW
1 stop with Southwest Airlines.
5h 23m
0-1 flights per day.
Tue & Wed
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Via Detroit DTW
1 stop with Delta Air Lines. 1-2 flights per day.

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5h 24m

Via Detroit DTW
1 stop with Delta Air Lines.
5h 24m
1-2 flights per day.
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Via Grand Rapids GRR
1 stop with Southwest Airlines. 0-1 flights per day.

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5h 35m

Via Grand Rapids GRR
1 stop with Southwest Airlines.
5h 35m
0-1 flights per day.
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Via Albuquerque ABQ
1 stop with Southwest Airlines. 0-1 flights per day.

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5h 35m

Via Albuquerque ABQ
1 stop with Southwest Airlines.
5h 35m
0-1 flights per day.
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Via Minneapolis MSP
1 stop with Delta Air Lines. 2 flights per day.

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5h 38m

Via Minneapolis MSP
1 stop with Delta Air Lines.
5h 38m
2 flights per day.
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Via Cincinnati CVG
1 stop with Southwest Airlines. 0-1 flights per day.
Begins in 5/10

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5h 40m

Begins in 5/10
Via Cincinnati CVG
1 stop with Southwest Airlines.
5h 40m
0-1 flights per day.
Begins in 5/10
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Via Tulsa TUL
1 stop with Southwest Airlines. 0-1 flights per day.

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5h 45m

Via Tulsa TUL
1 stop with Southwest Airlines.
5h 45m
0-1 flights per day.
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Via Oklahoma City OKC
1 stop with Southwest Airlines. 0-3 flights per day.

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6h 00m

Via Oklahoma City OKC
1 stop with Southwest Airlines.
6h 00m
0-3 flights per day.
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Via Columbus CMH
1 stop with Southwest Airlines. 1-2 flights per day.

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6h 08m

Via Columbus CMH
1 stop with Southwest Airlines.
6h 08m
1-2 flights per day.
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Via Dallas DFW
1 stop with Frontier Airlines. 0-1 flights per day.
Thu,Sat & Sun

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6h 20m

Thu,Sat & Sun
Via Dallas DFW
1 stop with Frontier Airlines.
6h 20m
0-1 flights per day.
Thu,Sat & Sun
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Via Dallas DAL
1 stop with Southwest Airlines. 5-7 flights per day.

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6h 30m

Via Dallas DAL
1 stop with Southwest Airlines.
6h 30m
5-7 flights per day.
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Via Louisville SDF
1 stop with Southwest Airlines. 0-1 flights per day.
Begins in 2/11

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6h 40m

Begins in 2/11
Via Louisville SDF
1 stop with Southwest Airlines.
6h 40m
0-1 flights per day.
Begins in 2/11
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Via Nashville BNA
1 stop with Southwest Airlines. 3-8 flights per day.

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6h 50m

Via Nashville BNA
1 stop with Southwest Airlines.
6h 50m
3-8 flights per day.
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1 stop route options with codeshare or different airlines:

Duration

Via Minneapolis MSP With United Airlines & Delta Air Lines 1-2 flights per day.

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8h 49m

Via Minneapolis MSP
8h 49m
With United Airlines & Delta Air Lines 1-2 flights per day.
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Find the best prices on hotels and car rental near Chicago Midway

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Denver to Chicago flights

There are over 21 airlines and as many as 317 flights every week to this destination. You can fly non-stop to Chicago (MDW) from Denver (DEN) with Southwest Airlines or Frontier Airlines but if a stopover option suits you better you can choose to fly via Indianapolis, Kansas City or any other of the 19 alternatives with connectiing airports.

Denver to Chicago with Southwest Airlines

You can fly non-stop every weekday with flights departing from 5:00 am to 10:00 pm. You can also catch a transit flight via Indianapolis or Kansas City.

With Delta Air Lines

If you choose to fly with Delta Air Lines from Denver to Chicago you can make a transit either via Detroit or via Minneapolis. The route via Detroit is 14 minutes faster. Delta Air Lines is a member of SkyTeam.

Distance & flight times: Denver International to Midway International Airport

The shortest flight time between DEN and MDW is 2 hours and 20 minutes.

ViaTotal flight timeLayover timeDistance
Direct2h 20m-898 miles (1445 km)
IND Indianapolis4h 48m1h 15m1141 miles (1836 km)
MCI Kansas City4h 55m45m939 miles (1511 km)
CLE Cleveland4h 55m40m1511 miles (2431 km)
MEM Memphis4h 55m1h 10m1358 miles (2185 km)
COS Colorado Springs5h 5m50m993 miles (1598 km)
STL Saint Louis5h 10m40m1024 miles (1648 km)
OMA Omaha5h 20m2h 30m897 miles (1443 km)
DTW Detroit5h 24m2h 38m1355 miles (2180 km)
GRR Grand Rapids5h 35m2h 30m1154 miles (1857 km)
ABQ Albuquerque5h 35m1h 10m1476 miles (2375 km)
MSP Minneapolis5h 38m2h 24m1032 miles (1660 km)
CVG Cincinnati5h 40m2h 5m1322 miles (2127 km)
TUL Tulsa5h 45m1h 40m1128 miles (1815 km)
OKC Oklahoma City6h 0m2h 25m1191 miles (1916 km)
CMH Columbus6h 8m1h 10m1442 miles (2320 km)
DFW Dallas6h 20m1h 52m1445 miles (2325 km)
DAL Dallas6h 30m3h 0m1452 miles (2336 km)
SDF Louisville6h 40m2h 55m1299 miles (2090 km)
BNA Nashville6h 50m2h 0m1413 miles (2274 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.DEN-MDW flight routesDenver to Chicago flight routes illustrated on a map.
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Departing from Denver International
Departing from Denver International. Copyright: Denver International Airport
Denver - Chicago route map and flight paths
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You can fly non-stop from Denver (DEN) to Chicago (MDW) with Southwest Airlines or Frontier Airlines. The flight takes approximately 2 hours and 20 minutes. If you travel with a connecting flight instead, for example via Indianapolis, the total flight time will be 4 hours and 48 minutes.

If you're interested in direct flights, Southwest Airlines or Frontier Airlines is available. For flights with stopovers, Southwest Airlines, Delta Air Lines or Frontier Airlines is also an option.

The flight time between Denver (DEN) and Chicago Midway International (MDW) is approximately 2 hours and 20 minutes. The distance between the two airports is 1032 miles (or 1660 kilometers).

Yes, you can fly non-stop to MDW from DEN with Southwest Airlines or Frontier Airlines.

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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