Flights from Chicago to San Jose (MDW → SJO)

MDW
Chicago
Chicago Midway International, USA
SJO
San Jose
Juan Santamaria International, Costa Rica
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No direct flights found. Here are the 17 fastest 1-stop options.
viaCancun(CUN)
MDW→CUN+1h 30mCUN→SJO
5h 42m
viaAtlanta(ATL)
MDW→ATL+1h 30mATL→SJO
5h 43m
viaTampa(TPA)
MDW→TPA+1h 30mTPA→SJO
5h 45m
viaOrlando(MCO)
MDW→MCO+1h 30mMCO→SJO
5h 49m
viaMiami(MIA)
MDW→MIA+1h 30mMIA→SJO
5h 51m
viaFort Lauderdale(FLL)
MDW→FLL+1h 30mFLL→SJO
5h 53m
viaCharlotte(CLT)
MDW→CLT+1h 30mCLT→SJO
5h 55m
viaHouston(HOU)
MDW→HOU+1h 30mHOU→SJO
6h 11m
viaHouston(IAH)
MDW→IAH+1h 30mIAH→SJO
6h 11m
viaDallas(DFW)
MDW→DFW+1h 30mDFW→SJO
6h 23m
viaBaltimore(BWI)
MDW→BWI+1h 30mBWI→SJO
6h 34m
viaNew York(EWR)
MDW→EWR+1h 30mEWR→SJO
7h 1m
viaGuadalajara(GDL)
MDW→GDL+1h 30mGDL→SJO
7h 32m
viaDenver(DEN)
MDW→DEN+1h 30mDEN→SJO
7h 46m
viaLas Vegas(LAS)
MDW→LAS+1h 30mLAS→SJO
9h 23m
viaLos Angeles(LAX)
MDW→LAX+1h 30mLAX→SJO
9h 58m
viaSan Francisco(SFO)
MDW→SFO+1h 30mSFO→SJO
10h 45m
Search all options on Kiwi.com → Total times include an estimated 90-minute layover. Actual times vary by airline and connection.

Frequently asked questions

Are there direct flights from Chicago to San Jose? Currently, there are no direct flights from MDW to SJO. You may need to connect through another airport.

Related guides for this route

Sibling pages from across Flightmaps — fares, visa rules, country aggregations, and per-airline routes for Chicago → San Jose.

Cheap flights from Chicago to San Jose Cheapest month to fly to San Jose Flights from USA Flights to Costa Rica Visa-free with USA passport All airports in Costa Rica

Try a nearby airport to Chicago

Flights to San Jose (SJO) from other airports within 350 km of Chicago. Often unlocks cheaper fares or better times.

ORD → SJO 25 km from MDW Chicago → San Jose USA · 282 destinations SBN → SJO 119 km from MDW South Bend → San Jose USA · 22 destinations RFD → SJO 121 km from MDW Rockford → San Jose USA · 8 destinations MKE → SJO 130 km from MDW Milwaukee → San Jose USA · 34 destinations BMI → SJO 175 km from MDW Bloomington → San Jose USA · 6 destinations

Or try a nearby airport to San Jose

Flights from Chicago (MDW) to other airports within 350 km of San Jose.

MDW → FON 67 km from SJO Chicago → Fortuna Costa Rica · 5 destinations MDW → ACO 104 km from SJO Chicago → Cobano Costa Rica · 5 destinations MDW → LIR 161 km from SJO Chicago → Guanacaste Costa Rica · 30 destinations MDW → MGA 321 km from SJO Chicago → Managua Nicaragua · 11 destinations

Other flights from Chicago (MDW)

Aguascalientes (AGU) Albany (ALB) Albuquerque (ABQ) Asheville (AVL) Atlanta (ATL) Austin (AUS) Baltimore (BWI) Birmingham (BHM) All 97 destinations →

Other flights from San Jose (SJO)

Amsterdam (AMS) Atlanta (ATL) Baltimore (BWI) Bocas Del Toro (BOC) Bogota (BOG) Cancun (CUN) Cartagena (CTG) Charlotte (CLT) All 55 destinations →