Flights from Orlando to Chicago (SFB → MDW)

SFB
Orlando
Orlando Sanford Intl, USA
MDW
Chicago
Chicago Midway International, USA
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No direct flights found. Here are the 18 fastest 1-stop options.
viaIndianapolis(IND)
SFB→IND+1h 30mIND→MDW
3h 20m
viaLouisville(SDF)
SFB→SDF+1h 30mSDF→MDW
3h 20m
viaKnoxville(TYS)
SFB→TYS+1h 30mTYS→MDW
3h 20m
viaAsheville(AVL)
SFB→AVL+1h 30mAVL→MDW
3h 22m
viaCincinnati(CVG)
SFB→CVG+1h 30mCVG→MDW
3h 22m
viaNashville(BNA)
SFB→BNA+1h 30mBNA→MDW
3h 23m
viaGrand Rapids(GRR)
SFB→GRR+1h 30mGRR→MDW
3h 39m
viaMemphis(MEM)
SFB→MEM+1h 30mMEM→MDW
3h 41m
viaPittsburgh(PIT)
SFB→PIT+1h 30mPIT→MDW
3h 47m
viaDes Moines(DSM)
SFB→DSM+1h 30mDSM→MDW
4h 13m
viaTulsa(TUL)
SFB→TUL+1h 30mTUL→MDW
4h 29m
viaOmaha(OMA)
SFB→OMA+1h 30mOMA→MDW
4h 34m
viaWichita(ICT)
SFB→ICT+1h 30mICT→MDW
4h 44m
viaOklahoma City(OKC)
SFB→OKC+1h 30mOKC→MDW
4h 48m
viaAlbany(ALB)
SFB→ALB+1h 30mALB→MDW
4h 50m
viaAustin(AUS)
SFB→AUS+1h 30mAUS→MDW
5h 13m
viaPunta Cana(PUJ)
SFB→PUJ+1h 30mPUJ→MDW
7h 16m
viaLas Vegas(LAS)
SFB→LAS+1h 30mLAS→MDW
8h 13m
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 Orlando to Chicago? Currently, there are no direct flights from SFB 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 Orlando → Chicago.

Cheap flights from Orlando to Chicago Cheapest month to fly to Chicago Flights from USA Flights to USA Visa-free with USA passport All airports in USA

Try a nearby airport to Orlando

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

MCO → MDW 39 km from SFB Orlando → Chicago USA · 172 destinations DAB → MDW 49 km from SFB Daytona Beach → Chicago USA · 11 destinations MLB → MDW 96 km from SFB Melbourne → Chicago USA · 5 destinations LAL → MDW 115 km from SFB Lakeland → Chicago USA · 9 destinations GNV → MDW 143 km from SFB Gainesville → Chicago USA · 7 destinations

Or try a nearby airport to Chicago

Flights from Orlando (SFB) to other airports within 350 km of Chicago.

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

Other flights from Orlando (SFB)

Akron (CAK) Albany (ALB) Allentown (ABE) Appleton (ATW) Asheville (AVL) Atlantic City (ACY) Austin (AUS) Bangor (BGR) All 67 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 →