Flights from Chicago to Guanacaste (MDW → LIR)
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viaAtlanta(ATL)
MDW→ATL+1h 30mATL→LIR
5h 38m
viaMiami(MIA)
MDW→MIA+1h 30mMIA→LIR
5h 50m
viaFort Lauderdale(FLL)
MDW→FLL+1h 30mFLL→LIR
5h 51m
viaCharlotte(CLT)
MDW→CLT+1h 30mCLT→LIR
5h 52m
viaHouston(IAH)
MDW→IAH+1h 30mIAH→LIR
6h 2m
viaHouston(HOU)
MDW→HOU+1h 30mHOU→LIR
6h 3m
viaDetroit(DTW)
MDW→DTW+1h 30mDTW→LIR
6h 5m
viaDallas(DFW)
MDW→DFW+1h 30mDFW→LIR
6h 15m
viaBaltimore(BWI)
MDW→BWI+1h 30mBWI→LIR
6h 32m
viaMinneapolis(MSP)
MDW→MSP+1h 30mMSP→LIR
6h 44m
viaPhiladelphia(PHL)
MDW→PHL+1h 30mPHL→LIR
6h 47m
viaNew York(EWR)
MDW→EWR+1h 30mEWR→LIR
6h 59m
viaBoston(BOS)
MDW→BOS+1h 30mBOS→LIR
7h 35m
viaDenver(DEN)
MDW→DEN+1h 30mDEN→LIR
7h 37m
viaLos Angeles(LAX)
MDW→LAX+1h 30mLAX→LIR
9h 48m
viaSan Francisco(SFO)
MDW→SFO+1h 30mSFO→LIR
10h 35m
viaSeattle(SEA)
MDW→SEA+1h 30mSEA→LIR
11h 3m
Frequently asked questions
Are there direct flights from Chicago to Guanacaste? Currently, there are no direct flights from MDW to LIR. 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 → Guanacaste.
Try a nearby airport to Chicago
Flights to Guanacaste (LIR) from other airports within 350 km of Chicago. Often unlocks cheaper fares or better times.
Or try a nearby airport to Guanacaste
Flights from Chicago (MDW) to other airports within 350 km of Guanacaste.