Boston to Chicago Flight Delays
Sample size: 20,086 BOS–ORD flights, January 2023 to December 2025 (BTS). 22.5% of Boston to Chicago flights arrived at least 15 minutes late. That is 1.7 points better than the 24.2% median for those routes, making this one of the steadier pairings in the network. Departure time moves the odds more than anything else on this route: 06:00 departures run 9.05% late against 42.79% for 17:00. Tuesday is the calmest day at 18.11%, Friday the worst at 25.42%. Cancellations (2024 to 2025) peak in January at 3.98% of scheduled flights and bottom out in September at 0.39%. Last updated: 2026-10-01.
These figures are historical US domestic rates, not a forecast for one departure. Use the AI delay predictor before you book.
BOS airport delay guide · ORD airport delay guide · Predict a BOS to ORD flight
Best time to fly BOS to ORD
The best time to fly BOS to ORD is the 6 AM departure and fly on a Tuesday, not a Friday (18.11% against 25.42%): 9.05% of 6 AM flights arrived 15+ minutes late, against 42.79% at 5 PM.
Lowest observed delay rates depart 05:00–06:00, 08:00. The highest sit at 17:00, 19:00–20:00. Only departure hours with at least 100 recorded flights are listed, so sparse hours are blank rather than estimated.
| Departure hour | Delayed 15+ min | Flights observed |
|---|---|---|
| 05:00 | 10.34% | 716 |
| 06:00 | 9.05% | 2,519 |
| 07:00 | 14.52% | 1,467 |
| 08:00 | 10.5% | 1,372 |
| 09:00 | 12.39% | 1,186 |
| 10:00 | 13.55% | 1,026 |
| 11:00 | 16.16% | 1,083 |
| 12:00 | 15.61% | 1,493 |
| 13:00 | 24.89% | 691 |
| 14:00 | 22.46% | 966 |
| 15:00 | 28.92% | 1,511 |
| 16:00 | 37.06% | 1,646 |
| 17:00 | 42.79% | 1,636 |
| 18:00 | 34.42% | 1,101 |
| 19:00 | 41.08% | 830 |
| 20:00 | 37.52% | 757 |
BOS to ORD flight time and distance
Scheduled gate-to-gate time from BOS to ORD is a median 2 h 57 min. Flights actually took a median 2 h 50 min gate to gate, including 2 h 13 min in the air. 3.9% ran 30 or more minutes over schedule and 67.6% arrived sooner than scheduled (BTS data, January 2023 to December 2025).
BOS to ORD is 867 miles (BTS data).
| Airline | Scheduled (median) | Actual (median) | In the air (median) | 30+ min over schedule | Flights |
|---|---|---|---|---|---|
| United Airlines | 2 h 54 min | 2 h 48 min | 2 h 12 min | 3.8% | 6,885 |
| American Airlines | 2 h 58 min | 2 h 49 min | 2 h 10 min | 3.7% | 4,848 |
| Delta Air Lines | 2 h 56 min | 2 h 51 min | 2 h 12 min | 3.5% | 2,851 |
| Republic Airways | 3 h 5 min | 2 h 56 min | 2 h 18 min | 5.0% | 1,789 |
| JetBlue Airways | 3 h | 2 h 53 min | 2 h 14 min | 3.8% | 1,686 |
| Envoy Air | 3 h 1 min | 2 h 52 min | 2 h 16 min | 4.5% | 1,429 |
| SkyWest Airlines | 2 h 59 min | 2 h 51 min | 2 h 15 min | 3.3% | 456 |
How late, and why
When a BOS to ORD flight was late (15+ minutes), it arrived an average of 80 minutes late (median 48). 9.4% of all completed flights arrived an hour or more late (BTS data, 2023 to 2025).
Of the delay minutes on late BOS to ORD flights, 41.7% were caused by a late incoming aircraft, 27.5% by the airline (crew, maintenance, ground handling), 26.4% by the air-traffic system (volume, non-extreme weather, airport operations), 4.2% by extreme weather and 0.0% by security (BTS data, 2023 to 2025).
| Cause | Share of delay minutes |
|---|---|
| late incoming aircraft | 41.7% |
| airline | 27.5% |
| air-traffic system | 26.4% |
| extreme weather | 4.2% |
| security | 0.0% |
BTS assigns causes to delay minutes on flights that arrived 15+ minutes late. "Air-traffic system" includes non-extreme weather that slows traffic.
BOS to ORD delays by day of week
| Day | Delayed 15+ min | Flights observed |
|---|---|---|
| Mon | 21.45% | 3,044 |
| Tue | 18.11% | 2,788 |
| Wed | 20.83% | 2,832 |
| Thu | 25.41% | 3,015 |
| Fri | 25.42% | 3,029 |
| Sat | 20.52% | 2,432 |
| Sun | 25.02% | 2,946 |
Month-by-month cancellation pattern
Share of scheduled BOS–ORD flights cancelled in each month, from BTS 2024–2025 on-time reporting. These are cancellations, not delays. Delay figures on this page cover January 2023 to December 2025.
| Month | Cancelled | Flights scheduled |
|---|---|---|
| Jan | 3.98% | 954 |
| Feb | 1% | 903 |
| Mar | 0.46% | 1,076 |
| Apr | 0.83% | 1,079 |
| May | 0.79% | 1,268 |
| Jun | 0.76% | 1,323 |
| Jul | 3.5% | 1,343 |
| Aug | 2.31% | 1,386 |
| Sep | 0.39% | 1,283 |
| Oct | 0.45% | 1,325 |
| Nov | 2.38% | 1,221 |
| Dec | 0.57% | 1,061 |
Airlines on BOS to ORD: delays and cancellations
United Airlines, American Airlines, Delta Air Lines, Republic Airways, JetBlue Airways and Envoy Air fly this route today. Only carriers with at least 200 scheduled flights on the pairing are listed. Delay rates cover January 2023 to December 2025; cancellation rates cover 2024 to 2025.
| Airline | Share of flights | Delayed 15+ min | Cancelled | Flights scheduled |
|---|---|---|---|---|
| United Airlines | 35% | 20.17% | 1.26% | 4,921 |
| American Airlines | 25% | 22.55% | 1.53% | 3,459 |
| Delta Air Lines | 13% | 28.87% | 1.29% | 1,860 |
| Republic Airways | 11% | 19.12% | 1.81% | 1,599 |
| JetBlue Airways | 9% | 25.5% | 0.86% | 1,286 |
| Envoy Air | 7% | 21.34% | 1.8% | 942 |
Related pages
- BOS delays: rate, worst hours and live risk
- ORD delays: rate, worst hours and live risk
- Boston to DC flights (BOS to DCA)
- DC to Boston flights (DCA to BOS)
- US airline cancellation rates
- Thanksgiving and Christmas 2026 flight delay guide
- Predict a BOS to ORD flight
Check your odds: Will my flight be delayed? · Will my flight be cancelled?
BOS vs ORD: airport conditions
Both ends of a route shape its delay profile. These are DelayGuard's operational scores for Boston and Chicago.
| Measure | BOS (Boston) | ORD (Chicago) |
|---|---|---|
| Congestion | high | high |
| Weather risk | moderate | high |
| NAS vulnerability | high | high |
| Average taxi-out | 16 min | 22 min |
| Runways | 6 | 8 |
BOS to ORD questions
- How long is the flight from Boston to Chicago?
- Scheduled gate-to-gate time from BOS to ORD is a median 2 h 57 min, and flights actually took a median 2 h 50 min including 2 h 13 min in the air. 3.9% ran 30+ minutes over schedule (BTS data, January 2023 to December 2025).
- How often do BOS to ORD flights get delayed?
- Across 20,086 recorded BOS–ORD departures, January 2023 to December 2025 (BTS), 22.5% arrived at least 15 minutes late. Departure time matters most: 6:00 departures run 9.05% late against 42.79% for 17:00. Actual delay frequency varies by airline, time of day, and season.
- What is the best time of year to fly BOS to ORD?
- Both Boston and Chicago share the same primary risk window: December–February (winter weather) and June–August (summer storms). Plan around those periods for the lowest delay probability on this route.
- Which airline is most reliable on BOS to ORD?
- On BOS→ORD, Republic Airways has the lowest measured delay rate at 19.12% of 1,789 flights, and Delta Air Lines the highest at 28.87% (BTS, January 2023 to December 2025). JetBlue Airways cancels the fewest at 0.86% (2024 to 2025). These are route-specific figures, not airline-wide averages.
- How late are BOS to ORD flights when they are delayed?
- When a BOS to ORD flight was late (15+ minutes), it arrived an average of 80 minutes late (median 48). 9.4% of all completed flights arrived an hour or more late (BTS data, 2023 to 2025).
- How accurate is DelayGuard's delay prediction for this route?
- DelayGuard's delay risk score comes from an ML model trained on BTS data (3.95 million US domestic flights, 2023 to mid-2025), with live weather data (within 5 days of departure) and FAA NAS advisories (within 6 hours) — a likelihood of delay, not a guarantee.
Delay figures reflect arrivals 15 or more minutes late in BTS on-time reporting. Cancellation figures are separate and count flights that never operated. Hours, days and months with fewer than 100 recorded flights are omitted rather than estimated.