Flights from Chicago (MDW)

Last updated: Oct 2, 2026

Chicago Midway International Airport is an airport serving Chicago, United States.

Right now there are 106 airports in 6 countries connected to Chicago, 92 of them domestic, with 15 airlines flying scheduled passenger traffic.

Chicago's longest nonstop connection is San Juan (SJU), 2,059 miles, offered by Southwest Airlines.

Airlines flying from Chicago

Southwest Airlines95 destinations
Frontier Airlines9 destinations
Volaris9 destinations
Air France3 destinations
Allegiant Air3 destinations
Delta Air Lines3 destinations
KLM3 destinations
Korean Air3 destinations
Virgin Atlantic3 destinations
WestJet3 destinations

AeroMexico1 destination
Air Transat1 destination
LATAM Chile1 destination
Porter Airlines1 destination
Sun Country1 destination

Show all 15 airlines

Popular destinations from Chicago

The places reachable from Chicago on the most scheduled services, busiest first.

Show top 20 destinations

Popular destinations with a stopover

Aside from the non-stop destinations above, these popular places require a connection:

Boise (BOI)United States
Reno (RNO)United States
Santa Ana (SNA)United States
Harlingen (HRL)United States
Spokane (GEG)United States
Greenville (GSP)United States
Midland (MAF)United States
Corpus Christi (CRP)United States
West Palm Beach (DJT)United States
Islip (ISP)United States

Lubbock (LBB)United States
Santa Barbara (SBA)United States
Eugene (EUG)United States
Fresno (FAT)United States
Santa Rosa (STS)United States

Show all 15 destinations

Information on Points & Miles

Distance matters when booking with points and miles: several loyalty programs price award flights in distance bands. Each list below adds the non-stop destinations from Chicago not already shown in a shorter great-circle distance band.

From Chicago, which places within 500 miles can I reach?

Show all 19 destinations

From Chicago, which places within 1,000 miles can I reach?

Show top 20 destinations

From Chicago, which places within 2,000 miles can I reach?

Show top 20 destinations

From Chicago, which places within 3,000 miles can I reach?

San Juan (SJU)2,059 mi

Flights from Chicago (MDW) by country

Chicago has nonstop service to 9 airports in Mexico: Cancun (CUN), San Luis Potosi (SLP), Morelia (MLM), Guadalajara (GDL), Durango (DGO), Aguascalientes (AGU), Silao (BJX), Zacatecas (ZCL), and San Jose del Cabo (SJD). Flights are offered by Frontier Airlines, Southwest Airlines, and Volaris.
Mexico9 destinations
You can fly nonstop from Chicago to Toronto (YTZ) in Canada with Air Transat and Porter Airlines.
Canada1 destination
You can fly nonstop from Chicago to Punta Cana (PUJ) in Dominican Republic with Southwest Airlines.
Dominican Republic1 destination
You can fly nonstop from Chicago to Montego Bay (MBJ) in Jamaica with Southwest Airlines.
Jamaica1 destination
You can fly nonstop from Chicago to San Juan (SJU) in Puerto Rico with Southwest Airlines.
Puerto Rico1 destination

Seasonal and upcoming routes from Chicago

Not flying yet

San Juan (SJU)Starts Nov 7, 2026
Montego Bay (MBJ)Starts Nov 21, 2026
Pensacola (PNS)Starts Nov 21, 2026
Punta Cana (PUJ)Starts Nov 21, 2026
Palm Springs (PSP)Feb 13, 2027 – Apr 3, 2027
Panama City Beach (ECP)Starts Mar 11, 2027
San Jose del Cabo (SJD)Mar 11, 2027 – Apr 5, 2027

Ending before the rest

Knoxville (TYS)Through Nov 29, 2026
Colorado Springs (COS)Through Jan 3, 2027
Dallas-Fort Worth (DFW)Through Apr 5, 2027

The other 80 routes are scheduled across the whole window the feed publishes.

Airline alliances from Chicago

SkyTeam3 destinations

Award programs flying from Chicago

How many of these destinations each program's airlines fly to. Reach, not award availability — that is a live fare question this schedule feed cannot answer.

Frontier Miles9 destinations
Club Premier3 destinations
Delta SkyMiles3 destinations
Flying Blue3 destinations
SAS EuroBonus3 destinations
Virgin Atlantic3 destinations

Domestic flights from Chicago

Show top 20 destinations

Alternative airports near Chicago

Chicago (ORD)15 mi / 24 km
Chicago/West Chicago (DPA)27 mi / 43 km
Chicago/Aurora (AUZ)37 mi / 60 km
Benton Harbor (BEH)72 mi / 116 km
South Bend (SBN)74 mi / 119 km

Frequently asked questions

What is the official name of airport MDW?

The airport's official name is Chicago Midway International Airport. On Roame and most flight schedules, you will find it under the code MDW.

What is the airport code for Chicago Midway International Airport?

The IATA airport code for Chicago Midway International Airport is MDW. Enter MDW in Flightmap whenever you want to use this exact airport.

Where is Chicago Midway International Airport (MDW)?

Chicago Midway International Airport serves Chicago, United States. Flightmap uses the airport's exact coordinates, so nearby airports and route distances stay tied to MDW, not just the broader city.

How can I explore flights from Chicago (MDW)?

Open the map with MDW as your departure airport and Anywhere as the destination. You can then narrow the routes by airline, alliance, aircraft, mileage program, nonstop service, and observed award fares.

Does Flightmap show direct and connecting flights from Chicago?

Yes. Flightmap separates nonstop routes from destinations that need a connection, and the Nonstop only control lets you focus on direct service from MDW.

Can I look for award flights from Chicago (MDW)?

Yes. When Roame has observed award availability for a route from MDW, signed-in members can see the lowest points price by cabin and the related carrier fees, then continue to the full award search.

How many places can I reach from Chicago (MDW)?

Current schedule data connects Chicago (MDW) with 106 connected airports in 6 countries. The route list can change as airlines publish new seasons, so the page is rebuilt from the latest available schedule aggregate.

Which airlines fly from Chicago (MDW)?

The current route data includes 15 airlines: AeroMexico, Air France, Air Transat, Allegiant Air, Delta Air Lines, Frontier Airlines, KLM, Korean Air, LATAM Chile, Porter Airlines, Southwest Airlines, Sun Country, Virgin Atlantic, Volaris, and WestJet. Use the airline filter to isolate any one of them on the map.

What is the longest nonstop connection from Chicago (MDW)?

The longest nonstop connection currently present in the route data is San Juan (SJU), about 2,059 miles from Chicago. It is offered by Southwest Airlines.

Are there domestic flights from Chicago (MDW)?

Yes. The current route data includes 92 domestic destinations within United States. The Domestic flights section highlights named airport links from that set.