Cheap flights from Chicago to Boston from £67
Trusted by millions
Kiwi.com Guarantee for stress-free travel
One search, all the best deals
Explore flight deals to Boston
Not happy with the results? Try some of our useful filters
Search by stops
Search by carrier
Search by price
Search by departure date
Not happy with the results? Try some of our useful filters
Search by stops
Search by carrier
Search by price
Search by departure date
How much do flights to Boston cost?
Getting from Boston's airport to the city center
Fastest options: Blue Line subway or taxi. Best value: MBTA Blue Line and Silver Line bus.
Transport Option | Typical Time | Typical Cost | Frequency | Best For |
|---|---|---|---|---|
10-15 min | $2.40 (CharlieCard fare) | every 5–10 min (traffic dependent) | budget travelers | |
15-25 min | $0 (free from airport to South Station) | every 8–15 min (traffic dependent) | free ride to South Station | |
7-15 min | $15-$22 (varies by operator and destination) | on-demand during operating hours (traffic dependent) | scenic harbor crossing | |
15-35 min | $25-$45 (metered; includes tunnel tolls and airport fee) | on-demand 24/7 (traffic dependent) | door-to-door convenience | |
15-35 min | $20-$50 (surge pricing may apply) | on-demand 24/7 (traffic dependent) | app-based booking | |
15-35 min | $50-$100 (pre-booked; varies by provider) | by reservation (traffic dependent) | groups or business travelers | |
15-40 min | $40-$100 (daily rate; parking extra in downtown) | on-demand (traffic dependent) | exploring beyond Boston |
Notes:
- Prices in USD; table created in 2025 and subject to change.
- The Silver Line SL1 is free when traveling from the airport to South Station; fare applies in the opposite direction.
- Free shuttle buses connect all airport terminals to the Blue Line Airport station and the rental car center.
- Taxi fares include a $2.75 airport fee and tunnel tolls; traffic can significantly affect journey times.
- We recommend checking official transport websites for your travel planning.
Updated: December 2025
Key info about flying to Boston
Weekly direct flights
Discover the top airlines offering direct flights from Chicago to Boston in the next month. You’ll find the number of daily direct flights per airline in the chart.
| Airline | Mon 04.05 | Tue 05.05 | Wed 06.05 | Thu 07.05 | Fri 08.05 | Sat 09.05 | Sun 10.05 |
|---|---|---|---|---|---|---|---|
| 9 | 6 | 8 | 10 | 10 | 4 | 4 | |
| 2 | 1 | 1 | 2 | 2 | 1 | 2 | |
| --- | --- | --- | --- | --- | --- | --- | |
| Weekly flights: 62 total | Daily flights: 8.86 average | Most flights: Thursday 10 flights |
| Airline | Mon 11.05 | Tue 12.05 | Wed 13.05 | Thu 14.05 | Fri 15.05 | Sat 16.05 | Sun 17.05 |
|---|---|---|---|---|---|---|---|
| 6 | 7 | 8 | 6 | 9 | 3 | 3 | |
| 2 | 1 | 1 | 2 | 1 | 1 | 1 | |
| --- | --- | --- | --- | --- | --- | --- | |
| Weekly flights: 51 total | Daily flights: 7.29 average | Most flights: Friday 9 flights |
| Airline | Mon 18.05 | Tue 19.05 | Wed 20.05 | Thu 21.05 | Fri 22.05 | Sat 23.05 | Sun 24.05 |
|---|---|---|---|---|---|---|---|
| 6 | 6 | 9 | 4 | 5 | 5 | 8 | |
| 2 | --- | 1 | 2 | 1 | --- | 1 | |
| --- | --- | --- | --- | --- | --- | --- | |
| Weekly flights: 50 total | Daily flights: 7.14 average | Most flights: Wednesday 9 flights |
| Airline | Mon 25.05 | Tue 26.05 | Wed 27.05 | Thu 28.05 | Fri 29.05 | Sat 30.05 | Sun 31.05 |
|---|---|---|---|---|---|---|---|
| 2 | 5 | 9 | 10 | 10 | 6 | 5 | |
| --- | 2 | 2 | 2 | 2 | 1 | --- | |
| --- | --- | --- | --- | 10 | --- | --- | |
| Weekly flights: 66 total | Daily flights: 9.43 average | Most flights: Thursday 10 flights |
Check-in for a flight from Chicago to Boston
| Name | Carrier code | IATA Code | Passport needed during booking |
|---|---|---|---|
| Frontier Airlines | FFT | F9 | No |
| JetBlue Airways | JBU | B6 | No |
| Allegiant Air | AAY | G4 | No |
| United Airlines | UAL | UA | No |
| WestJet | WJA | WS | No |
Online check-in is not available for these airlines.
Weather in Boston
Average Weather
| Month | Average monthly max temperature | Average monthly min temperature |
| January | 1°C | -4°C |
| February | 3°C | -4°C |
| March | 7°C | 0°C |
| April | 12°C | 5°C |
| May | 18°C | 10°C |
| June | 23°C | 15°C |
| July | 27°C | 19°C |
| August | 27°C | 18°C |
| September | 22°C | 14°C |
| October | 16°C | 9°C |
| November | 10°C | 3°C |
| December | 5°C | 0°C |
14 day forecast
Boston travel tips
Get ready for high accommodation prices in Boston
Accommodation in Boston is one of the main travel expenses, as staying in the city is really very expensive. In summer, a bed in a 6-bed dorm costs around $60 per night. A private room in a 2-star hotel will cost from $170 in peak season and from $100 in the low season. If you’re low on budget, it’s better to book a room on Airbnb – a private room starts at $65 per night.
Enjoy the architecture of the Boston Public Library at Copley square
The Boston Public Library is built in the style of the Italian Renaissance palaces. Spend time looking at the vaults of this fantastic building! Sometimes you can get inside even if you are not a Boston resident — check the schedule and activities on the library’s website.
Grab some sweets at legendary Boston bakery, Mike's Pastry
Sweet teeth will certainly appreciate Mike's Pastry bakery, famous for its cannoli with cream. The venue first opened its doors in 1946 and since then has earned the recognition of both locals and former US President Bill Clinton. On average, the prices for cakes here range from $3-5.
Frequently asked questions
Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any origin and destination in the world by plane. Find the cheapest routes and best deals, as well as the best dates to travel.
Explore alternative trips
Flights from Chicago
Flights to Boston
Popular routes
Airports near Chicago
Airports near Boston
Download our app