Boston (BOS) to Chicago (MDW)
Flight time
≈ 2h 31m
Bearing
273° W
Boston (BOS) to Chicago (MDW) is 858 miles (1,381 km) as the crow flies — the great-circle baseline most distance-based mileage programs credit.
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What actually flies BOS–MDW
Filed traffic dataIn May 2026, Southwest Airlines operated the most departures, one of 2 carriers flying nonstop BOS–MDW; the Boeing 737 MAX 8 was the most common aircraft at 56% of departures; flights ran 87% full.
Departures
246
May 2026
Seats
42,073
both directions
Passengers
36,728
both directions
Load factor
87.3%
RPM ÷ ASM
Who flies BOS–MDW?
Southwest Airlines operated the most nonstop BOS–MDW departures in May 2026 (245), one of 2 carriers on the route.
- WN
245 departures · 42,001 seats
Share of departures99.6%87.3%
Load
- DL
1 departures · 72 seats
Share of departures0.4%87.5%
Load
What plane flies BOS–MDW?
In May 2026, the Boeing 737 MAX 8 flew 56% of BOS–MDW departures — more than any other aircraft type.
- Boeing 737 MAX 8
137 departures · 87.0% load
55.7% - Boeing 737-800
85 departures · 87.5% load
34.5% - Boeing 737-700
23 departures · 88.5% load
9.3% - Boeing 757-200
1 departures · 87.5% load
0.4%
How has BOS–MDW traffic changed?
Nonstop BOS–MDW departures fell from 314 in June 2025 to 246 in May 2026.
Monthly nonstop BOS–MDW traffic, trailing 12 months through May 2026. Bars scale to the busiest month; months with no filed service show as zero.
June 2025
314 departures · 46,742 passengers
88.0%
Load
July 2025
340 departures · 51,321 passengers
89.7%
Load
August 2025
267 departures · 41,659 passengers
93.5%
Load
September 2025
254 departures · 36,852 passengers
87.3%
Load
October 2025
276 departures · 40,994 passengers
89.2%
Load
November 2025
168 departures · 24,969 passengers
85.7%
Load
December 2025
183 departures · 25,734 passengers
83.0%
Load
January 2026
133 departures · 16,811 passengers
73.7%
Load
February 2026
120 departures · 15,282 passengers
75.6%
Load
March 2026
221 departures · 29,945 passengers
82.0%
Load
April 2026
238 departures · 33,421 passengers
82.7%
Load
May 2026
246 departures · 36,728 passengers
87.3%
Load
By direction
Each direction is filed separately — they rarely match.
BOS → MDW
84.9% full
123 departures · 17,631 passengers
MDW → BOS
89.7% full
123 departures · 19,097 passengers
Nonstop BOS–MDW traffic has been filed since 2025.
Source: US DOT BTS Form 41 T-100 Segment (All Carriers). Data through May 2026; filings from 2025. Public domain (US Government work).
The airports
Frequently asked
How far is Boston (BOS) from Chicago (MDW)?
BOS to MDW is 858 miles (1,381 km / 746 nautical miles) measured great-circle — the shortest path over the surface of the Earth.
How long is the flight from BOS to MDW?
A nonstop covers the 858-mile great-circle distance in roughly 2h 31m of block time, before winds. Actual schedules vary a few percent by direction and aircraft.
What plane flies BOS–MDW?
In May 2026, the Boeing 737 MAX 8 flew the largest share of departures (55.7%), followed by the Boeing 737-800 (34.5%).
What mileage do I earn flying BOS–MDW?
Distance-based programs credit off the 858-mile great-circle figure, then apply your fare-class earning rate. Revenue-based programs credit off the fare instead.
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