About flights from Chicago (MDW)
Midway gets underestimated. Most people default to O'Hare when they think of flying out of Chicago, but MDW has its own loyal following — and for good reason. It's smaller, easier to get through, and Southwest Airlines basically built a home here, which means competitive fares and a solid domestic network. I've passed through plenty of mid-size American airports, and Midway hits a sweet spot between manageable chaos and genuine connectivity. You're not fighting a megahub, but you're not limited either.
Quick stats for MDW
- Direct destinations: 97
- Countries served: 6
- Continents reached: 1 of 6
- Average flight distance: 1,578 km
- Longest non-stop: San Juan (SJU) — 3,313 km (~4h 8m)
- Shortest non-stop: Milwaukee (MKE) — 130 km (~10 min)
- Reach score: 67/99
Why fly to Chicago?
Ninety-seven direct destinations sounds modest until you realize how well-curated the network actually is. Southwest dominates the domestic routes — 85 of them across the U.S. — so if you're hopping between American cities, MDW is often the cheaper, less stressful option. The international reach leans Caribbean and Latin America, which honestly makes sense given Chicago's demographics and appetite for winter escapes. That San Juan route stretching 3,313 km is the longest you'll find here, and it's consistently popular. Mexico has eight direct connections, covering resort towns and border cities alike. It's not a globe-spanning hub, but for North American travel, it punches well.
Longest non-stop flights from MDW
The furthest destinations you can reach non-stop from Chicago:
- San Juan, Puerto Rico (SJU) — 3,313 km, approximately 4h 8m
- Punta Cana, Dominican Republic (PUJ) — 3,168 km, approximately 3h 58m
- San Francisco, USA (SFO) — 2,980 km, approximately 3h 44m
- Oakland, USA (OAK) — 2,961 km, approximately 3h 42m
- San Jose, USA (SJC) — 2,951 km, approximately 3h 41m
Short-haul flights from MDW
Quick getaway options with the shortest flights from Chicago:
- Milwaukee, USA (MKE) — 130 km, approximately 10 min
- Grand Rapids, USA (GRR) — 219 km, approximately 16 min
- Indianapolis, USA (IND) — 261 km, approximately 20 min
- Detroit, USA (DTW) — 365 km, approximately 27 min
- Cincinnati, USA (CVG) — 400 km, approximately 30 min
Top countries by direct connections from MDW
Chicago Midway International connects to 6 countries. Here are the most served:
- USA — 85 destinations (Albany, Albuquerque, Asheville, Atlanta and 81 more)
- Mexico — 8 destinations (Aguascalientes, Cancun, Durango, Guadalajara and 4 more)
- Jamaica — 1 destination (Montego Bay)
- Dominican Republic — 1 destination (Punta Cana)
- Puerto Rico — 1 destination (San Juan)
- Canada — 1 destination (Toronto)
Where to fly from Chicago
Flights to USA
Chicago has 85 direct routes to USA:
- Milwaukee (MKE) — 130 km
- Grand Rapids (GRR) — 219 km
- Indianapolis (IND) — 261 km
- Detroit (DTW) — 365 km
- Cincinnati (CVG) — 400 km
- Saint Louis (STL) — 405 km
- ...and 79 more destinations
Flights to Mexico
Chicago has 8 direct routes to Mexico:
- Cancun (CUN) — 2,308 km
- San Luis Potosi (SLP) — 2,496 km
- Durango (DGO) — 2,502 km
- Zacatecas (ZCL) — 2,518 km
- Aguascalientes (AGU) — 2,616 km
- Leon/Guanajuato (BJX) — 2,647 km
- ...and 2 more destinations
Flights to Jamaica
Chicago has 1 direct route to Jamaica:
- Montego Bay (MBJ) — 2,752 km
Tips for travelers at MDW
The Orange Line is your best friend. Chicago's L train connects MDW directly to the Loop in about 25 minutes for a couple of dollars — no surge pricing, no traffic surprises. Rideshares exist but downtown traffic can genuinely ruin your day. Winter is the real variable here. Lake-effect weather hits hard between December and February, so build buffer time into connections and check your flight status the night before. Summer is busy with leisure travelers, especially on those Caribbean routes, so book early if you're heading to Jamaica or Puerto Rico and want a decent fare.
Airlines operating from MDW
The following airlines offer non-stop flights from Chicago Midway International:
DL, F9, G4, PD, WN, Y4
Frequently asked questions about flying to Chicago
What's the best way to get from Midway Airport to downtown Chicago?
The Orange Line CTA train is your most affordable option at just $5 and takes about 40 minutes to the Loop, or you can grab a rideshare for $15-25 depending on traffic.
When is the best time to fly to or from Chicago Midway?
Midweek flights (Tuesday-Thursday) tend to be cheaper than weekends, and traveling in shoulder seasons like April-May or September-October usually offers better fares than summer and winter holidays.
How many destinations can I fly to directly from Midway?
Midway offers 97 direct destinations, so you've got plenty of non-stop options for both domestic and international travel without needing a connection.
Do I need a visa to enter the USA through Midway?
It depends on your citizenship—many countries participate in the ESTA program for visa-free entry, but others require a traditional visa, so check with the U.S. State Department website before your trip.
What's a helpful tip for Midway Airport?
Midway is smaller and less crowded than O'Hare, so it's generally quicker to get through security and baggage claim—just arrive about 2 hours early for domestic flights to stay comfortable.
Is flying into Midway cheaper than O'Hare?
Midway flights are often $20-50 cheaper per ticket since it's less busy, plus the Orange Line train to downtown is affordable, making it a budget-friendly alternative to Chicago's larger airport.
Plan your trip from Chicago
Browse the complete list of 97 destinations below to find your next flight from Chicago Midway International. Each route page includes distance, estimated flight time, and airline information to help you plan your trip.