Browse and Book

Las Vegas (Harry Reid International, LAS) to Chicago (ORD or MDW) is a competitive domestic route served by Southwest, Spirit, Frontier, United, American, and Delta. The cheapest flights from Las Vegas to Chicago are typically available in January, February, and September. Book 3–5 weeks ahead and fly on Tuesdays or Wednesdays for the best fares. Flight time is approximately 3 hours 30 minutes to 3 hours 45 minutes. Fares can start as low as $59 one-way on budget carriers when booked well in advance.

Nonstop flights from Seattle-Tacoma International Airport (SEA) to Chicago O'Hare (ORD) take approximately 3 hours 45 minutes to 4 hours. Alaska Airlines, United, Delta, and American operate nonstop service on this route. Alaska Airlines offers the highest frequency from SEA. One-way fares typically start from around $89–$150 when booked in advance.

Chicago Midway International Airport (MDW) is primarily served by Southwest Airlines, which uses it as a hub for domestic routes. To book flights to Chicago Midway, search directly on Southwest's website (as their fares don't always appear on third-party platforms) or use Triwize to compare available carriers. MDW is located closer to downtown Chicago than O'Hare and is served by the CTA Orange Line, making it convenient for many travellers. Spirit and other carriers also serve Midway on select routes.

United Airlines uses Chicago O'Hare (ORD) as one of its major hubs, offering the widest selection of nonstop domestic and international routes. To unlock the cheapest United flights to Chicago, use flexible date searching on Triwize or United's own website, look for Basic Economy fares (note these have restricted baggage and change policies), and book at least 3–5 weeks ahead for domestic routes. United also runs regular sales for MileagePlus members — signing up is free and sale fares are often exclusive to members.

Nonstop flights from Charlotte Douglas International Airport (CLT) to Chicago O'Hare (ORD) take approximately 2 hours to 2 hours 15 minutes. American Airlines operates the most frequent nonstop service on this route, as Charlotte is a major American hub. United, Delta, and Spirit also serve this route. One-way fares from Charlotte to Chicago start from around $69–$130 when booked in advance.

Nonstop flights from San Diego International Airport (SAN) to Chicago O'Hare (ORD) are operated by United, American, Delta, Southwest, and Spirit. Flight time is approximately 3 hours 45 minutes to 4 hours. Economy fares on this route typically range from $89–$200 one-way when booked 3–5 weeks ahead. Cheapest fares are usually available in January, February, and September. Budget carriers Spirit and Frontier offer the lowest base fares, though add-on fees for bags and seat selection should be factored in.

Boston Logan International Airport (BOS) to Chicago O'Hare (ORD) is a popular transcontinental route served by American, United, Delta, JetBlue, and Spirit. Flight time is approximately 2 hours 45 minutes to 3 hours. To book the cheapest Boston to Chicago flights, use Triwize to search across a flexible date window, fly on Tuesdays or Wednesdays, and book 4–6 weeks in advance. JetBlue and Spirit often offer the lowest base fares on this route. Fares from Boston to Chicago start from around $79–$140 one-way.

Nonstop flights from Philadelphia International Airport (PHL) to Chicago O'Hare (ORD) take approximately 2 hours 15 minutes to 2 hours 30 minutes. American Airlines operates the most frequent nonstop service, as Philadelphia is a major American hub. United, Delta, and Spirit also offer service on this route. Economy fares from Philadelphia to Chicago typically start from around $69–$120 one-way when booked in advance.