Boston to Chicago (Midway) Flights
Everything you need to know about the BOS → MDW domestic route — flight time, airlines, fares, and booking tips. Track your flight in real time with TripTrack.
✈️ Route Overview
Key facts for the Boston to Chicago (Midway) route
🛫 Airlines on This Route
Carriers operating BOS → MDW flights
| Airline | Notes |
|---|---|
| Delta | SkyMiles frequent flyer program |
| American Airlines | AAdvantage frequent flyer program |
| United | MileagePlus frequent flyer program |
| Southwest | Rapid Rewards — bags fly free |
| Alaska Airlines | Mileage Plan — generous earning rates |
| JetBlue | TrueBlue — free snacks, above-average legroom |
💡 Booking Tips
How to get the best deal on Boston to Chicago (Midway) flights
Best Days to Fly
Wednesday and Saturday departures often have the best prices
Fare Range
$80-$240 round trip. Book 3–6 weeks in advance for domestic routes, 2–3 months for international.
Red-Eye Flights
✗ Not available
No overnight options on this route — plan for daytime travel.
Track Your Flight
Once booked, TripTrack automatically imports your flight from your confirmation email. Real-time gate changes and delay alerts — no manual entry needed.
🧳 Travel Tips for This Route
Practical advice from frequent travelers on the BOS → MDW route
- 1 Early morning flights have the lowest cancellation/delay rates.
- 2 Book 3–6 weeks in advance for the best domestic fares.
🏢 Airport Guides
Full terminal, transit, and traveler info for both airports
Track Your BOS → MDW Flight — Automatically
TripTrack monitors your flight in real time — gate changes, delays, and departure updates sent to your phone the moment they happen. Connect your Gmail once and your trips appear automatically. No manual entry.
Frequently Asked Questions — Boston to Chicago (Midway) Flights
How long is the flight from Boston to Chicago (Midway)?
The average flight time from Boston (BOS) to Chicago (Midway) (MDW) is 2h 20m. This is an estimate including taxi, climb, and descent time — actual flight time may vary based on winds and routing.
Which airlines fly from Boston to Chicago (Midway)?
Airlines operating the BOS to MDW route include Delta, American Airlines, United and 3 more. Check each airline's website for current schedules and availability.
How far is Boston from Chicago (Midway)?
The great-circle distance from Boston to Chicago (Midway) is 858 miles (1,381 km). This is the straight-line distance — actual flight paths may be slightly longer.
What are the cheapest days to fly from Boston to Chicago (Midway)?
Wednesday and Saturday departures often have the best prices. Fares on this route typically range $80-$240 round trip.
Is there a time zone change flying from Boston to Chicago (Midway)?
Yes — there is a -1 hour when flying from Boston to Chicago (Midway). TripTrack automatically shows local times for both your departure and arrival airports.
Are there red-eye flights from Boston to Chicago (Midway)?
No, there are currently no overnight (red-eye) flights on the BOS to MDW route. All flights operate during daytime hours.
How can I track my Boston to Chicago (Midway) flight in real time?
TripTrack automatically tracks your BOS to MDW flight — showing real-time gate changes, delays, and departure updates. Connect your Gmail once and your booking confirmation is imported automatically. Available free on iOS and Android.