Direct flights from Boston to Chicago (BOS → MDW)

Distance 1,379 km (857 mi)
Est. duration 1h 37m
BOS
Boston
Boston Logan International Airport, USA
MDW
Chicago
Chicago Midway International, USA
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Live fares · BOS → MDW

Available flights

Southwest AirlinesNon-stop
from$174
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Frequently asked questions

How far is the flight from Boston to Chicago? The flight distance from BOS to MDW is approximately 1,379 km (857 miles).
How long is the flight from BOS to MDW? The estimated flight time from Boston to Chicago is approximately 1h 37m.
What airlines fly from BOS to MDW? Airlines operating direct flights from Boston to Chicago include: WN.

Cheapest fares Boston → Chicago

Boston BOS
Chicago MDW
May from $94 June from $90 July from $90 August — September — October from $112

Related guides for this route

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

Cheap flights from Boston 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 Boston

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

MHT → MDW 71 km from BOS Manchester → Chicago USA · 15 destinations ORH → MDW 71 km from BOS Worcester → Chicago USA · 5 destinations PVD → MDW 79 km from BOS Providence → Chicago USA · 38 destinations PSM → MDW 81 km from BOS Portsmouth → Chicago USA · 6 destinations HYA → MDW 99 km from BOS Hyannis → Chicago USA · 8 destinations

Or try a nearby airport to Chicago

Flights from Boston (BOS) to other airports within 350 km of Chicago.

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

Other flights from Boston (BOS)

Abu Dhabi (AUH) Amsterdam (AMS) Anchorage (ANC) Anguilla (AXA) Aruba (AUA) Asheville (AVL) Athens (ATH) Atlanta (ATL) All 153 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 →