Flights from Chicago to San Jose Cabo (MDW → SJD)

MDW
Chicago
Chicago Midway International, USA
SJD
San Jose Cabo
Los Cabos International, Mexico
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No direct flights found. Here are the 20 fastest 1-stop options.
viaDallas(DFW)
MDW→DFW+1h 30mDFW→SJD
4h 57m
viaKansas City(MCI)
MDW→MCI+1h 30mMCI→SJD
4h 57m
viaSaint Louis(STL)
MDW→STL+1h 30mSTL→SJD
4h 57m
viaAustin(AUS)
MDW→AUS+1h 30mAUS→SJD
5h 1m
viaHouston(IAH)
MDW→IAH+1h 30mIAH→SJD
5h 8m
viaHouston(HOU)
MDW→HOU+1h 30mHOU→SJD
5h 10m
viaNashville(BNA)
MDW→BNA+1h 30mBNA→SJD
5h 22m
viaDenver(DEN)
MDW→DEN+1h 30mDEN→SJD
5h 27m
viaMinneapolis(MSP)
MDW→MSP+1h 30mMSP→SJD
5h 31m
viaPhoenix(PHX)
MDW→PHX+1h 30mPHX→SJD
5h 36m
viaGuadalajara(GDL)
MDW→GDL+1h 30mGDL→SJD
5h 37m
viaLeon/Guanajuato(BJX)
MDW→BJX+1h 30mBJX→SJD
5h 39m
viaDetroit(DTW)
MDW→DTW+1h 30mDTW→SJD
5h 44m
viaAtlanta(ATL)
MDW→ATL+1h 30mATL→SJD
5h 49m
viaLas Vegas(LAS)
MDW→LAS+1h 30mLAS→SJD
6h 10m
viaSalt Lake City(SLC)
MDW→SLC+1h 30mSLC→SJD
6h 12m
viaCharlotte(CLT)
MDW→CLT+1h 30mCLT→SJD
6h 14m
viaSan Diego(SAN)
MDW→SAN+1h 30mSAN→SJD
6h 17m
viaOntario(ONT)
MDW→ONT+1h 30mONT→SJD
6h 24m
viaLos Angeles(LAX)
MDW→LAX+1h 30mLAX→SJD
6h 33m
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 Cabo? Currently, there are no direct flights from MDW to SJD. 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 Cabo.

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

Try a nearby airport to Chicago

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

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

Or try a nearby airport to San Jose Cabo

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

MDW → LAP 121 km from SJD Chicago → La Paz Mexico · 9 destinations MDW → LMM 288 km from SJD Chicago → Los Mochis Mexico · 6 destinations MDW → CUL 290 km from SJD Chicago → Culiacan Mexico · 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 Cabo (SJD)

Atlanta (ATL) Austin (AUS) Baltimore (BWI) Calgary (YYC) Charlotte (CLT) Chicago (ORD) Culiacan (CUL) Dallas (DFW) All 54 destinations →