Midwest

Cheap Flights from Chicago: Book Airline Tickets

Compare 51 flight routes from Chicago, from short hops of about 180 miles to long trips of about 8,040 miles. Each route page lists the airports at both ends, the distance, a typical flight time and the time difference. For a price on your dates, ask a specialist. Planning a trip into town instead? See flights to Chicago.

Airports to compare in Chicago

ORD · O'Hare International
A major hub for connecting traffic and long-haul flights, with a direct train to downtown.
MDW · Midway International
Closer to downtown and served by its own train line, with a focus on shorter domestic routes.

Flights from Chicago within the United States and nearby

ORD ⇄ IND Chicago to Indianapolis 180 mi · about 1 h ORD ⇄ DTW Chicago to Detroit 230 mi · about 1 h 15 min ORD ⇄ CVG Chicago to Cincinnati 260 mi · about 1 h 15 min ORD ⇄ STL Chicago to St. Louis 260 mi · about 1 h 15 min ORD ⇄ CMH Chicago to Columbus 300 mi · about 1 h 15 min ORD ⇄ CLE Chicago to Cleveland 310 mi · about 1 h 15 min ORD ⇄ MSP Chicago to Minneapolis 330 mi · about 1 h 30 min ORD ⇄ MCI Chicago to Kansas City 400 mi · about 1 h 30 min ORD ⇄ BNA Chicago to Nashville 410 mi · about 1 h 30 min ORD ⇄ PIT Chicago to Pittsburgh 410 mi · about 1 h 30 min ORD ⇄ BUF Chicago to Buffalo 470 mi · about 1 h 45 min ORD ⇄ MEM Chicago to Memphis 490 mi · about 1 h 45 min ORD ⇄ DCA Chicago to Washington, DC 590 mi · about 2 h ORD ⇄ CLT Chicago to Charlotte 600 mi · about 2 h ORD ⇄ ATL Chicago to Atlanta 610 mi · about 2 h ORD ⇄ RDU Chicago to Raleigh-Durham 650 mi · about 2 h ORD ⇄ PHL Chicago to Philadelphia 680 mi · about 2 h ORD ⇄ JFK Chicago to New York 740 mi · about 2 h 15 min ORD ⇄ DFW Chicago to Dallas 800 mi · about 2 h 15 min ORD ⇄ MSY Chicago to New Orleans 840 mi · about 2 h 30 min ORD ⇄ BOS Chicago to Boston 860 mi · about 2 h 30 min ORD ⇄ JAX Chicago to Jacksonville 870 mi · about 2 h 30 min ORD ⇄ DEN Chicago to Denver 890 mi · about 2 h 30 min ORD ⇄ IAH Chicago to Houston 930 mi · about 2 h 30 min ORD ⇄ AUS Chicago to Austin 980 mi · about 2 h 45 min ORD ⇄ MCO Chicago to Orlando 1,010 mi · about 2 h 45 min ORD ⇄ TPA Chicago to Tampa 1,010 mi · about 2 h 45 min ORD ⇄ SAT Chicago to San Antonio 1,040 mi · about 2 h 45 min ORD ⇄ ABQ Chicago to Albuquerque 1,120 mi · about 3 h ORD ⇄ RSW Chicago to Fort Myers 1,120 mi · about 3 h ORD ⇄ FLL Chicago to Fort Lauderdale 1,180 mi · about 3 h ORD ⇄ MIA Chicago to Miami 1,200 mi · about 3 h 15 min ORD ⇄ SLC Chicago to Salt Lake City 1,250 mi · about 3 h 15 min ORD ⇄ PHX Chicago to Phoenix 1,440 mi · about 3 h 45 min ORD ⇄ LAS Chicago to Las Vegas 1,510 mi · about 3 h 45 min ORD ⇄ SAN Chicago to San Diego 1,720 mi · about 4 h 15 min ORD ⇄ SEA Chicago to Seattle 1,720 mi · about 4 h 15 min ORD ⇄ PDX Chicago to Portland 1,730 mi · about 4 h 15 min ORD ⇄ LAX Chicago to Los Angeles 1,740 mi · about 4 h 15 min ORD ⇄ SMF Chicago to Sacramento 1,780 mi · about 4 h 15 min ORD ⇄ SFO Chicago to San Francisco 1,840 mi · about 4 h 30 min ORD ⇄ HNL Chicago to Honolulu 4,240 mi · about 9 h 15 min

International flights from Chicago

ORD ⇄ YYZ Chicago to Toronto 440 mi · about 1 h 45 min ORD ⇄ CUN Chicago to Cancun 1,450 mi · about 3 h 45 min ORD ⇄ LHR Chicago to London 3,940 mi · about 8 h 45 min ORD ⇄ CDG Chicago to Paris 4,140 mi · about 9 h ORD ⇄ FCO Chicago to Rome 4,810 mi · about 10 h 15 min ORD ⇄ HND Chicago to Tokyo 6,290 mi · about 13 h 15 min ORD ⇄ DXB Chicago to Dubai 7,230 mi · about 15 h 15 min ORD ⇄ DEL Chicago to Delhi 7,470 mi · about 15 h 45 min ORD ⇄ BOM Chicago to Mumbai 8,040 mi · about 16 h 45 min

Getting to the airport

CTA trains run from both airports to the city center, which is usually the most predictable option at busy times.

Airlines with a base in Chicago

United Airlines, American Airlines, Southwest Airlines. Having a base usually means more flights and more connecting options, though not every route is nonstop.

Frequently asked questions

Which airport should I use for flights from Chicago?

Chicago is served by ORD, MDW. With several airports, compare total price, schedule and ground travel from each. See choosing an airport.

What are popular routes from Chicago?

Popular routes on this site include New York, Los Angeles, Atlanta, Dallas and Miami. All routes work in both directions.

When is the best time to fly from Chicago?

Late spring through early fall is the most pleasant stretch. Winter brings snow and cold that can cause delays.

Do you list fares here?

No. A specialist checks live availability for your dates and confirms the full price before payment.

Route list updated October 18, 2026.