Direct flights from Chicago to Boston (MDW → BOS)

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

Available flights

Southwest AirlinesNon-stop
from$146
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Frequently asked questions

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

Cheapest fares Chicago → Boston

Chicago MDW
Boston BOS
May from $94 June from $90 July from $109 August — September — October —

Related guides for this route

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

Cheap flights from Chicago to Boston Cheapest month to fly to Boston 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 Chicago

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

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

Or try a nearby airport to Boston

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

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

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