Flights operate between Chicago (MDW) and Boston (BOS).
1 airline operates this route with 2-6 flights daily flights.
Average flight time is 2h 10m - 2h 20m.
Route distance is 863 miles (1389 km).
Route Distance
863 miles (1389 km)
Average Duration
2h 10m - 2h 20m
Airlines Operating This Route
Southwest Airlines
Flight Frequency
Daily Flights
2-6 flights
Weekly Flights
21
Typical Departure Time Ranges
Earliest Departure
05:30
Latest Departure
19:50
Route Intelligence Dashboard
Overall Connectivity Score
70
GoodRoute Diversity
1
Direct Routes
Southwest Airlines serves 1 destination from MDW
Weekly Frequency
28
Weekly Flights
Trend: Stable
Top 1 Most Frequent Routes - Details
| Route | Weekly Flights | Duration | Distance | Reliability |
|---|---|---|---|---|
| MDW → Boston (BOS) (BOS) | 28/week | 2h 10m - 2h 20m | 863 km | Moderate |
Flight Schedule & Filters
Southwest Airlines flights from Chicago (MDW) to Boston (BOS)
Southwest Airlines operates scheduled nonstop flights between Chicago (MDW) and Boston (BOS). Southwest Airlines operates 2-6 flights daily flights on this route.• Flight Duration: 2h 10m - 2h 20m (average flight time)• Distance: 863 miles (1389 km) (air miles between airports)• Daily Flights: 2-6 flights (scheduled departures per day)
Chicago (MDW)
US
Boston (BOS)
US
FLIGHT TIME
2h 10m - 2h 20m
FLIGHT DISTANCE
863 miles (1389 km)
2h 15m - 2h 15m
05:30
19:50
863 miles (1389 km)
February
1 (Show)
21
Southwest Airlines Terminal Information & Contact
Departure Terminal - Chicago (MDW)
Terminal: 1
Phone: 800-435-9792
Location: 1, Chicago, US
Arrival Terminal - Boston (BOS)
Terminal: B
Phone: 800-435-9792
Location: B, Boston, US
Southwest Airlines Flight Schedule from Chicago (MDW) to Boston (BOS)
| Flight | Airline | Departure | Arrival | Aircraft |
|---|---|---|---|---|
WN4825 |  Southwest Airlines | 05:30 | 08:45:00 | Boeing 737MAX 8 Passenger |
WN3678 | Southwest Airlines | 09:35 | 12:50:00 | Boeing 737MAX 8 Passenger |
WN3680 | Southwest Airlines | 16:05 | 19:20:00 | Boeing 737MAX 8 Passenger |
WN1773 | Southwest Airlines | 19:50 | 23:05:00 | Boeing 737-700 (winglets) Passenger/BBJ1 |
Southwest Airlines Monthly Flight Calendar
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Southwest Airlines Terminal Information
Departure Terminal at Chicago (MDW):
• Terminal : Southwest Airlines operates from this terminal
Terminal 1:
• Southwest Airlines Terminal Phone: 800-435-9792
Arrival Terminal at Boston (BOS):
Terminal B:
• Southwest Airlines Terminal Phone: 800-435-9792
Weather & Climate at Boston (BOS)
11.4°C
Avg Temperature115mm
Avg Rainfall13.9km/h
Avg Wind Speed74%
Avg HumidityBest Months to Visit
Challenging Months
12-Month Weather Overview
Wind Speed by Month
Humidity by Month
Best Time to Book Flights to Boston (BOS)
Best Booking Window
Book 2-3 months in advance for best prices
Booking Tip
Avoid booking during extreme weather months for better deals
Peak Travel Months
Expect higher prices and more crowds during these months. Book early to secure better rates.
Recommended Months
These months offer the best balance of weather, prices, and availability.
Monthly Booking Recommendations
Flight Price Trends for Boston (BOS)
Cheapest Months to Fly
Book flights during these months for the best deals and lowest prices.
Most Expensive Months
Prices are typically highest during these months. Consider booking well in advance or choosing alternative dates.
Price Trend Analysis
Prices are typically lower during shoulder seasons
Monthly Price Trends
Best Months to Fly Southwest Airlines to Boston (BOS)
Shoulder Season
Transition periods with moderate conditions. Good balance of price and experience.
Challenging Months
These months may have less favorable conditions. Plan accordingly and book early.
Seasonal Insight
Best travel months: Year-round
Seasonal Travel Calendar
Southwest Airlines Contact Information and Customer Services
Southwest Airlines Address
2702 Love Field Dr
Dallas, TX 75235, US
Customer Service Phone
800-435-9792Official Website
southwest.com/Frequently Asked Questions
How many Southwest Airlines flights operate from Chicago (MDW) to Boston (BOS)?
Southwest Airlines operates 4 flights from Chicago (MDW) to Boston (BOS).
What city does Boston (BOS) airport serve?
Boston (BOS) airport serves Boston, US.
How long is the Southwest Airlines flight from Chicago (MDW) to Boston (BOS)?
The flight duration is approximately 2h 10m - 2h 20m.
What is the distance from Chicago (MDW) to Boston (BOS)?
The distance is 863 miles (1389 km).
What aircraft does Southwest Airlines use on this route?
Southwest Airlines uses Boeing 737MAX 8 Passenger, Boeing 737-700 (winglets) Passenger/BBJ1 on this route.
What are the earliest and latest Southwest Airlines flight departure times?
The earliest Southwest Airlines flight departs at 05:30 and the latest departs at 19:50.
Which terminal does Southwest Airlines use at Chicago (MDW)?
Southwest Airlines flights from Chicago (MDW) depart from Terminal 1. Terminal 1 phone: 800-435-9792.
View all Southwest Airlines flights to Chicago (MDW) →
Popular Southwest Airlines routes from Chicago include multiple destinations.
Route data verified regularly by Triposia Travel Research Team.