What is the fastest way from Boston to Chicago?

Fly, about 4h 20m (estimate; check the operator).

What is the cheapest way from Boston to Chicago?

Bus, from about 55 USD (estimate).

Boston to Chicago

6 ways to get from Boston to Chicago by fly, drive, train, bus.

FastestFly · 4h 20m

Lowest priceBus · ≈ 55 USD

Distance1,617 km

Filter & sort

Outbound: Boston → Chicago 2026-10-28

Fly Boston Logan → Chicago MidwayBestFastest

Door to door via BOS and MDW airports

››4h 20m

from 143 USDCached fareBook ↗

Estimate · 2 transfers · 1,365 kmSteps & map ›

Fly Laurence G Hanscom Field → Chicago Midway

Door to door via BED and MDW airports

››4h 45m

from 138 USDCached fareBook ↗

Estimate · 2 transfers · 1,365 kmSteps & map ›

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Fly Boston Logan → Chicago O'Hare

Door to door via BOS and ORD airports

››4h 51m

from 138 USDCached fareBook ↗

Estimate · 2 transfers · 1,365 kmSteps & map ›

Drive 1,596 km

Via I 80, I 84, I 80; I 90

18h 47m

≈ 128–255 USDEstimateBook ↗

Live routing · Direct · 1,596 kmSteps & map ›

Train Boston → Chicago Union Station + 1 connection

Orange Line › 449 › 126 · MBTA, Amtrak · State → Michigan & Van Buren/Ida B. Wells

›22h 45m

≈ 82–341 USDEstimateBook ↗

Departs12:57from Boston, local time

Timetable · 2 transfers · 1,613 kmSteps & map ›

Bus Boston (South Station) → Cleveland Bus Station (Brook Park)Cheapest

11 › Greyhound US0171 › Greyhound US0164 · MBTA, Greyhound-us · Chauncy St @ Summer St → Michigan & Van Buren/Ida B. Wells

23h 00m

≈ 55–164 USDEstimateBook ↗

Departs12:30from Boston (South Station), local time

Timetable · 3 transfers · 1,617 kmSteps & map ›

Prices marked Estimate are calculated from distance and are not quotes. Timetables come from open data and may change. Cached fares are recent prices found by Aviasales users, not live quotes. Always confirm with the operator. Partner links may earn us a commission at no extra cost to you. Learn more