Boston to Chicago nonstop
Yes: Southwest flies direct from Boston (BOS) to Chicago (MDW) about 4 times a day, year-round.
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- Distance and flight time
- 861 miles nonstop, about 2 hr 20 min gate to gate. Flight time is an estimate from the great-circle distance; the filings carry distance, not scheduled elapsed time.
- Seasonality
- Flew every month of the last year: busiest in July 2026 (33 flights a week), quietest in February 2026 (15 flights a week).
- Sep 2025: 29 flights a week
- Oct 2025: 31 flights a week
- Nov 2025: 20 flights a week
- Dec 2025: 20 flights a week
- Jan 2026: 15 flights a week
- Feb 2026: 15 flights a week
- Mar 2026: 25 flights a week
- Apr 2026: 28 flights a week
- May 2026: 28 flights a week
- Jun 2026: 32 flights a week
- Jul 2026: 33 flights a week
- Aug 2026: 31 flights a week
Flights a week by month, Sep 2025 to Aug 2026, from US DOT on-time filings. - Who operates the flights
- Southwest is the only carrier filing this pair.
- Fares
- Half of the 2,843 tickets in the US DOT fare survey for Q2 2025 sold between $75 and $200 one way, median $125. The survey runs a couple of quarters behind, so read it as the shape of the route's pricing rather than today's quote.
- Jul to Sep (Q3 2024): median $125 one way, middle half $100 to $200, 3,080 tickets
- Oct to Dec (Q4 2024): median $150 one way, middle half $100 to $225, 2,595 tickets
- Jan to Mar (Q1 2025): median $125 one way, middle half $75 to $200, 1,455 tickets
- Apr to Jun (Q2 2025): median $125 one way, middle half $75 to $200, 2,843 tickets
Jul to Sep, Jan to Mar and Apr to Jun trips were the cheapest (median $125 one way) and Oct to Dec trips cost the most (median $150), in the DOT ticket survey for Q3 2024 to Q2 2025. Bars show the middle half of one-way fares; the mark is the median.
Flying the other way? Chicago to Boston nonstop.
Other airports near Boston with nonstops to Chicago
Within about 100 miles of Boston Logan International Airport
Also nonstop from Boston (BOS)
Busiest other routes out of the same airport
- Chicago (ORD) about 25 times a day
- Washington (DCA) about 23 times a day
- New York (LGA) about 20 times a day
- San Francisco (SFO) about 16 times a day
- Atlanta (ATL) about 15 times a day
- Los Angeles (LAX) about 15 times a day
- Philadelphia (PHL) about 14 times a day
- New York (JFK) about 13 times a day
Staying in Chicago?
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