Cheap Flights from Denver to Chicago — $59

The Denver — Chicago route is served by multiple airlines, including United Airlines and Frontier Airlines. This is convenient for those who want the best balance of price, schedule, and travel conditions. Tickets start from $59, and depending on season and promotions, even better deals may appear. With our service, you can easily compare available options and book tickets that match your plans. The variety of carriers allows flexible choices and comfortable travel without overpaying.

Denver International Airport (DEN) is the region’s major international hub with a mix of full-service and low-cost carriers, so fares can range from budget-friendly to premium depending on carrier and season. Located about 25 miles (40 km) northeast of downtown Denver, the airport is connected by the RTD A Line commuter rail (roughly 37–45 minutes to Union Station) and by shuttles, ride-shares or taxis (30–60 minutes depending on traffic), with shuttle fares and public-transit tickets typically costing much less than private rides. Pros include extensive flight options, plentiful amenities and consistent schedules; cons can be longer transfer times and occasional congestion due to its distance from the city center.

Chicago is served primarily by two commercial airports with distinct roles. O’Hare International (ORD) is the city’s major international and connecting hub, typically handling most long-haul and legacy-carrier flights (United, American, and numerous global carriers). It sits about 17–20 miles northwest of downtown; travel by Blue Line + transfer or shuttle can take roughly 40–60 minutes, with rideshares and taxis usually costing more. Pros: extensive route network and frequent service; cons: can be busy and spread out, so connections may require longer walks. Midway Airport (MDW), about 10–13 miles southwest of the Loop, is often a budget- and leisure-focused alternative with many low-cost and domestic flights (frequent carriers include Southwest). Transit options include the Orange Line to downtown in roughly 25–35 minutes and rideshares/taxis at lower typical fares than O’Hare. Pros: smaller terminals and quicker processing for many travelers; cons: fewer international routes and fewer late-night options. Both airports offer rental cars and shuttle services; choice usually depends on route, price sensitivity, and convenience preferences.

In different months, ticket prices from Denver to Chicago vary: minimum — $93 (May 2026), maximum — $115 (March 2026). Typically, the flight costs $105–$105.