Cheap Flights from Denver to Chicago — $41

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.

Fly from Denver to Chicago with confidence—our search scans over 700 airlines, 50+ agencies, and more than 5 top booking systems to uncover the best prices, schedules, and ticket conditions for your trip. Friendly, fast results help you compare nonstop and connecting options so you can book the ideal flight to the Windy City in minutes.

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.

Fly nonstop from Denver to Chicago for the quickest, most convenient way to get between two vibrant U.S. hubs — fewer hassles, no layovers, and more time on the ground enjoying your destination. While connecting options can sometimes cost less, a direct flight saves hours and delivers a more comfortable travel experience, so book the nonstop that fits your schedule and priorities.

The route Denver — Chicago is served by many carriers — 4 in total, including Southwest Airlines, United Airlines, Frontier Airlines, and American Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $41) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.

We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Denver to Chicago