Boston to Chicago Flight Tickets
Compare the best flight deals from Boston to Chicago
About Boston - Chicago Flights
Find the best prices for flights between Boston (United States) and Chicago (United States) on Tripuck. We compare prices from hundreds of airlines to offer you the best options.
Boston has 2 airports, while Chicago has 6 airports. Compare flights between all airports to find the best deal.
Cheapest Months for Boston - Chicago Flights
Best month to fly
March 2026 - 2,733 ₺
March 2026
2,733 ₺
Direct
CheapestJune 2026
2,902 ₺
Direct
May 2026
2,996 ₺
Direct
April 2026
3,483 ₺
Direct
| Ay | Flight Type | Price |
|---|---|---|
| March 2026Cheapest | Direct | 2.733 ₺ |
| June 2026 | Direct | 2.902 ₺ |
| May 2026 | Direct | 2.996 ₺ |
| April 2026 | Direct | 3.483 ₺ |
Prices may change. Based on recent searches.
Airlines on Boston - Chicago Route
Boston Airports
Chicago Airports
Alternative Routes
Boston - Chicago Flight Summary
Cheaper tickets are usually available on weekdays and with early bookings.
Boston and Chicago - Airport Transportation
Logan International Airport (BOS)
How to Get to the Airport
Metro: You can reach Airport Station from the city center with the MBTA Blue Line and then take a free shuttle to the terminal. The journey takes approximately 15-20 minutes. Services run every 5-8 minutes and operate between 05:00-00:30.
Bus: You can reach the airport from South Station with the SL1 bus. The journey takes about 20 minutes, and services depart every 8-12 minutes.
Taxi: You can call a taxi from any point in the city center to reach the airport. The journey takes 15-30 minutes depending on traffic. Taxi service is available 24/7.
Uber/Lyft: You can use the Uber or Lyft app from the city center to select a drop-off point at the airport. The journey takes 15-30 minutes depending on traffic, and service is available 24/7.
Private Transfer: Private transfer or shuttle services from the city center to Logan Airport can be used with a reservation. The journey takes 20-40 minutes, and service frequency is determined by reservation.
O'Hare International Airport (ORD)
From Airport to City Center
Metro/Train: The CTA Blue Line Train is the most convenient option for transportation from O'Hare International Airport to downtown Chicago. The airport station is directly connected to Terminals 1, 2, and 3. Access from Terminal 5 is possible via a free shuttle train. The journey takes approximately 40-45 minutes. Services operate 24 hours a day, with trains running every 5-10 minutes during peak hours.
Bus (CTA and Private Shuttles): Buses connecting O'Hare Terminals 1, 2, 3, and 5 operate routes to downtown. The journey time varies between 45-60 minutes depending on traffic conditions. Services run every 15-30 minutes and generally operate from 5:00 AM to 11:45 PM.
Taxi: Official taxi stands at O'Hare are located at each terminal exit and provide direct transportation to downtown. The journey time varies between 30-60 minutes depending on traffic. Taxi services are available 24 hours a day.
Airport App-Based Rides (Uber/Lyft): Apps like Uber and Lyft operate in designated pickup areas at O'Hare. Journey time and cost can vary based on traffic and demand.
Car Rental: Various car rental companies are available at the airport. Car rental options can be arranged at offices located at terminal exits or at rental centers accessible via shuttle services.