Flights from San Jose to Chicago (SJO → MDW)

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

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

Try a nearby airport to San Jose

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

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

Or try a nearby airport to Chicago

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

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

Other flights from Chicago (MDW)

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