$44 Cheap Flights from Denver to Chicago

It’s prudent to find out about any quarantine requirements and travel advice reports in effect in your destination city. Be sure to check out our Covid-19 Travel Advisor for up-to-date info on booking a flight to Chicago Airport.

The only thing standing between you and your next incredible adventure is a single flight. Southwest Airlines is the only air carrier that offers direct services from DEN to Midway Intl. Airport (MDW), so it’s wise to book well in advance.

For more info about changing your flight to Midway Airport, please visit our Customer Service Portal.

If you were hoping to squeeze in a decent snooze during your Denver to Chicago trip, you may have to leave it till another time. The normal flight time between DEN and Midway Airport is only 2 hours and 17 minutes — just enough to get comfortable and rest your eyes for a short while.

With only 890 mi separating DIA airport and Midway Intl. Airport (MDW), you won’t have long between the seat belt sign flicking off and the captain preparing the wheels for touchdown.

Wanting to fly straight from Denver to Chicago? Southwest Airlines (WN) offers as many as 234 flights every month and is the number one choice for many seasoned travelers.

From the moment you enter the departure terminal to when you leave the arrivals terminal, if you’re flying with Southwest Airlines, Delta or Volaris you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.

This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.

Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.

Trying to figure out how early you should book your flight? It’s possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.