Direct flights from San Diego to Chicago (SAN → MDW)

Distance 2,778 km (1,726 mi)
Est. duration 3h 16m
SAN
San Diego
San Diego International Airport, USA
MDW
Chicago
Chicago Midway International, USA
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Live fares · SAN → MDW

Available flights

Southwest AirlinesNon-stop
from$298
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Frequently asked questions

How far is the flight from San Diego to Chicago? The flight distance from SAN to MDW is approximately 2,778 km (1,726 miles).
How long is the flight from SAN to MDW? The estimated flight time from San Diego to Chicago is approximately 3h 16m.
What airlines fly from SAN to MDW? Airlines operating direct flights from San Diego to Chicago include: WN.

Cheapest fares San Diego → Chicago

San Diego SAN
Chicago MDW
May from $207 June from $198 July — August — September — October —

Related guides for this route

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

Cheap flights from San Diego to Chicago Cheapest month to fly to Chicago Flights from USA Flights to USA Visa-free with USA passport All airports in USA WN routes & destinations All routes by this carrier

Try a nearby airport to San Diego

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

TIJ → MDW 29 km from SAN Tijuana → Chicago Mexico · 40 destinations SNA → MDW 122 km from SAN Santa Ana → Chicago USA · 48 destinations PSP → MDW 137 km from SAN Palm Springs → Chicago USA · 30 destinations LGB → MDW 149 km from SAN Long Beach → Chicago USA · 18 destinations ONT → MDW 152 km from SAN Ontario → Chicago USA · 31 destinations

Or try a nearby airport to Chicago

Flights from San Diego (SAN) to other airports within 350 km of Chicago.

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

Other flights from San Diego (SAN)

Albuquerque (ABQ) Amsterdam (AMS) Anchorage (ANC) Atlanta (ATL) Austin (AUS) Baltimore (BWI) Boise (BOI) Boston (BOS) All 87 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 →