Chicago to Boston Flight Tickets
Compare the best flight deals from Chicago to Boston
About Chicago - Boston Flights
Find the best prices for flights between Chicago (United States) and Boston (United States) on Tripuck. We compare prices from hundreds of airlines to offer you the best options.
Chicago has 6 airports, while Boston has 2 airports. Compare flights between all airports to find the best deal.
Cheapest Months for Chicago - Boston Flights
Best month to fly
November 2026 - 4.679 ₺
November 2026
4.679 ₺
Direct
CheapestOctober 2026
6.515 ₺
1 stops
June 2027
7.048 ₺
Direct
| Ay | Flight Type | Price |
|---|---|---|
| November 2026Cheapest | Direct | 4.679 ₺ |
| October 2026 | 1 stops | 6.515 ₺ |
| June 2027 | Direct | 7.048 ₺ |
Prices may change. Based on recent searches.
Popular Chicago - Boston Flights
Chicago - Boston
Boston - Chicago
Airlines on Chicago - Boston Route
| Havayolu | Uçuş Tipi | Fiyat |
|---|---|---|
| Southwest Airlines | Direct | 4.679 ₺ |
| Frontier Airlines | 1 stops | 6.515 ₺ |
Chicago Airports
Boston Airports
Alternative Routes
Alternative Routes from Chicago
Chicago - Boston Flight Summary
Direct flights from Chicago to Boston take approximately 2 hours 15 minutes. Airlines serving this route include American Airlines, JetBlue, United Airlines. Cheaper tickets are usually available on weekdays and with early bookings.
Chicago and Boston - Airport Transportation
Chicago Midway International Airport (MDW)
How to Get to the Airport
Metro/Train: From the Orange Line stations in the Loop area, you can board trains marked with Midway on the direction signs. The journey takes approximately 25 minutes, and the frequency varies between about 3–15 minutes depending on the time of day. Operating hours from the Loop to MDW are weekdays 03:55–01:30, Saturdays 04:25–01:30, and Sundays and holidays 04:25–01:30.
Bus: Since there is no direct regular bus option from the city center to MDW, the Orange Line is generally used. The N62 Archer line can be used for airport access; however, this bus operates throughout the night and its route does not go directly to the Loop. Therefore, a transfer may be necessary.
Taxi: You can reach the airport by calling a taxi from taxi stands or app-based services in the city center. Travel time may vary between 20-30 minutes depending on traffic conditions.
Uber/Bolt: You can reach the airport by calling a vehicle through the Uber or Bolt app in the city center. Vehicles will be waiting for you in designated areas. Travel time may vary depending on traffic density.
Car Rental: You can also choose car rental services to reach the airport from the city center. You can head directly to MDW with the vehicle you rented.
O'Hare International Airport (ORD)
How to Get to the Airport
Metro/Train: You can reach the airport in 40-45 minutes by taking the CTA Blue Line train from downtown Chicago. Services run every 5-15 minutes and operate 24 hours a day.
Bus: You can reach the airport by taking buses departing from downtown bus stops (e.g., around Union Station). The journey takes approximately 45-60 minutes, with buses departing every 15-30 minutes.
Taxi: Transportation from downtown Chicago to O'Hare by taxi is possible. The journey takes 30-60 minutes depending on traffic, and taxis operate 24 hours a day.
Airport App-Based Rides (Uber/Lyft): You can reach O'Hare from downtown via Uber or Lyft. You can request a ride through the app and board at designated pickup points.
Car Rental: You can reach the airport by renting a car from rental offices located in the city center. Information on rental procedures can be obtained from rental offices at the airport.
Logan International Airport (BOS)
From Airport to City Center
Metro: The MBTA Blue Line can be used for transportation from the airport to the city center. You can take a free shuttle from the terminal to Airport Station and then board the metro. The journey takes approximately 15-20 minutes. Services run every 5-8 minutes and operate between 05:00-00:30.
Bus: You can reach South Station (city center) with the Silver Line SL1 bus. Buses with stops in front of each terminal reach the center in about 20 minutes. Services depart every 8-12 minutes and operate between 05:00-01:00.
Taxi: Taxis to the city center can be found at official taxi stands at terminal exits. The journey takes 15-30 minutes depending on traffic. Taxi service operates 24/7.
Uber/Lyft: You can call Uber or Lyft from designated Ride App pickup areas. The journey takes 15-30 minutes depending on traffic. The apps offer service 24/7.
Private Transfer: Private transfer or shuttle services can be reserved from Logan Airport to the city center. The journey takes approximately 20-40 minutes, and services are arranged according to reservation.