Cheap Flights from Dallas to Chicago — $100

The Dallas — Chicago route is served by a wide range of airlines: 4 in total, including United Airlines, American Airlines, Southwest Airlines, and Frontier Airlines. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $100. Our service helps compare all available offers within seconds and choose the most convenient option. You can filter flights by price, departure time, or baggage rules to make your trip as comfortable as possible. With so many airlines, there’s always a chance to catch special promotions and save.

The distance between Dallas and Chicago is 1294km (802 miles). There are 229 direct flights from Dallas to Chicago. Dallas and Chicago are in the same time zone. Flights from Dallas begin at 5:00 AM. The latest flight from Dallas departs at 10:50 PM

Dallas is served primarily by two airports with different roles. Dallas/Fort Worth International (DFW) is a major international and connecting hub for full-service carriers, typically offering a wide range of long-haul and domestic flights and often positioning as mid-to-premium in terms of service and facilities. It sits roughly 20–25 miles northwest of downtown Dallas; travel by taxi or rideshare can take 25–45 minutes depending on traffic, while the DART Orange Line plus Trinity Railway Express can take about 40–60 minutes, with fares commonly falling in the low single-digit to low-double-digit range. Pros: extensive route network, many amenities. Cons: large layout can mean long transfers and higher ground-transport costs at peak times. Dallas Love Field (DAL) functions more as a domestic, budget-leaning airport and is typically dominated by low-cost and leisure carriers. Located about 6 miles northwest of downtown, it usually offers quicker access for city travelers: taxis or rideshares often take 15–25 minutes, local buses and the DART system provide connections that can take 20–40 minutes, and fares are generally modest. Pros: compact terminal and short walking times. Cons: fewer international routes and limited long-haul options compared with the larger DFW hub.

O'Hare International Airport (ORD) is Chicago's primary global hub, serving many full-service carriers and acting as a major connection point for both domestic and international flights. It typically handles most premium and long-haul services, while fares can be mid-to-high depending on season and carrier. ORD sits about 17 miles northwest of downtown; passengers usually reach the city by CTA Blue Line trains (roughly 45–60 minutes, low single-digit fares), airport shuttles and rideshares (30–50 minutes, variable cost), or taxis (around 35–60 minutes). Pros: extensive route network and frequent schedules; cons: large layout and occasional delays can make transfers less convenient. Midway Airport (MDW) is Chicago's smaller, more budget- and leisure-oriented airport, often favored by low-cost carriers and short-haul domestic itineraries. It can offer lower fares than the larger hub, particularly on point-to-point routes, though prices vary by demand. Midway lies about 10 miles southwest of downtown; typical connections include the CTA Orange Line (25–35 minutes, economical fare), shuttle services and rideshares (20–40 minutes, cost varies), or taxis (25–45 minutes). Pros: compact terminals and quicker transfers; cons: fewer international routes and limited late-night options compared with the main hub.