Good to know - Cheap tickets Chicago — Boston
| Cheapest flight found | $34 |
|---|---|
| Minimal flight time | 1h 59m |
| Flight distance | 1366 km |
| Most popular airline | Southwest Airlines |
Airfare Chicago – Boston by month
Here you can find out in what months how much a ticket Chicago – Boston costs to buy cheap plane tickets.
| Month | One-way | Round-trip |
|---|---|---|
| March 2026 | ||
| January 2026 | ||
| December 2025 | ||
| November 2025 | ||
| October 2025 | ||
| September 2025 | ||
| August 2025 | ||
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Remember that the optimal time for booking air tickets is 59 days before the departure date, this is the average time at which air tickets were sold at the lowest prices.
Schedule of direct flights Chicago — Boston
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 05:05 | 08:15 | tue, wed | WN3787 | Southwest Airlines | 2h 10m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 05:30 | 08:45 | mon, thu, fri | WN404 | Southwest Airlines | 2h 15m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 06:00 | 09:15 | mon, thu, fri, sat, sun | WN1427 | Southwest Airlines | 2h 15m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 06:00 | 09:26 | mon, thu, fri, sun | UA2104 | United Airlines | 2h 26m | O'Hare International Airport — Logan International Airport | Select dates |
| 06:01 | 09:26 | mon | UA2104 | United Airlines | 2h 25m | O'Hare International Airport — Logan International Airport | Select dates |
| 06:25 | 09:49 | daily | AA4106 | American Airlines | 2h 24m | O'Hare International Airport — Logan International Airport | Select dates |
| 06:30 | 09:56 | sat | UA2104 | United Airlines | 2h 26m | O'Hare International Airport — Logan International Airport | Select dates |
| 06:45 | 10:08 | wed, thu, fri | AA4106 | American Airlines | 2h 23m | O'Hare International Airport — Logan International Airport | Select dates |
| 06:50 | 10:05 | sun | WN1915 | Southwest Airlines | 2h 15m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 07:00 | 10:31 | daily | DL1602 | Delta Air Lines | 2h 31m | O'Hare International Airport — Logan International Airport | Select dates |
Popular airlines flying Chicago — Boston
Flight Chicago – Boston is served by 42 airlines. 6 airlines operate direct flights.
Airlines with direct flights
Other airlines flying with transfers
- Aer Lingus (EI)
- Aeromexico (AM)
- Air Canada (AC)
- Air France (AF)
- Alaska Horizon (Washington State Cougars Livery) (AS)
- Allegiant Air (G4)
- Amazon Air (GB)
- Apex Logistics (5Y)
- Austrian Airlines (OS)
- Avianca (AV)
- Breeze Airways (MX)
- British Airways (BA)
- Cape Air (9K)
- Cathay Pacific (Oneworld Livery) (CX)
Sales of tickets from Chicago to Boston in the last 48 hours
Dynamics airfare Chicago — Boston by month for the last year
according to LowCost.Club for the last year
The airfare depends on the departure date. Our chart shows the low season prices on route Chicago — Boston
The graph shows that booking flights Chicago — Boston is best planned for July and flights Chicago — Boston — Chicago in the month of November.
Flights Chicago — Boston
The selection of cheap flights Chicago — Boston
Here you can find and purchase the cheapest flights Chicago — Boston from $34 and Chicago — Boston — Chicago from $20.
The price of the flight Chicago — Boston (United States) — Chicago from $20 (round-trip).
The average price of the flight Chicago — Boston (United States) — Chicago $261 (round-trip).
- Departure city: Chicago
- IATA code of the city of origin: CHI
- Departure airports: Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport
- Departure country: United States
- Destination city: Boston
- IATA code of the destination city: BOS
- Destination airports: Pease Air Force Base, Logan International Airport, Boston City Heliport
- Destination country: United States
Low cost flights Chicago — Boston (CHI — BOS)
The distance between Chicago and Boston 849 miles (or 1366 kilometres).
The time difference between Chicago and Boston is 1 h.
Minimal flight time from Chicago to Boston 1h 59m.
LowCostClub always do a comparison of airfares Chicago — Boston with several airlines (include Southwest Airlines, United Airlines, American Airlines). They will always give you all available options so you can find the cheapest flight to Boston. In addition, you can choose the platform where you want to place your orders. There are also special offers for air tickets Chicago — Boston. Last week, for instance, the cheapest round-trip prices stood at $20 while the cheapest one-way price that was available within the last week cost $34
Routes from nearby cities to Boston
A flight from a neighbouring city can help you save money on plane tickets.
The most frequent flight to Boston is from Grand Rapids. The cheapest airfare can be purchased with a flight from Madison from $59. The nearest airports from Chicago with a flight to Boston are in Fort Wayne.
Popular International routes from Chicago
Popular routes from Boston
If you are going to fly from Boston, then study the popular flights. The most popular flights from Boston:
Popular domestic routes from Chicago
FAQ about Chicago — Boston
Are there any direct flights Chicago — Boston?
Yes, they do: WN3787, WN404, WN1427, UA2104, AA4106, WN1915, DL1602, AA3821, UA2067, WN3786, WN171, AA547, AA1080, B6312, DL5719, UA721, UA3752, WN5421, AA630, WN1669, DL1371, DL2570, WN2630, UA399, AA2837, AA1271, WN1011, UA580, DL972, DL2677, DL2679, UA2138, WN3273, AA4766, AA3160, UA1677, B61012, AA1461, WN3170, UA1989, WN1933, WN1132, DL2646, AA3107, B62312, WN937, , UA1129, UA8229, UA2444, AA4796, AA4650, AA4404, AA2682, UA1495, UA1779
Can we fly from Chicago to Boston?
Yes, you can fly from Chicago to Boston. Chicago has 8 airports (Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport) for flights. Southwest Airlines, United Airlines, American Airlines, Delta Air Lines, JetBlue, Jet Linx Aviation depart from Chicago on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through Aer Lingus, Aeromexico, Air Canada, Air France, Alaska Horizon (Washington State Cougars Livery), Allegiant Air, Amazon Air, Apex Logistics, Austrian Airlines, Avianca, Breeze Airways, British Airways, Cape Air, Cathay Pacific (Oneworld Livery), Copa Airlines, DHL, Emirates, Etihad Airways, FedEx, Frontier (Cubby the Bear Livery), Iberia, Icelandair, ITA Airways, Japan Airlines, Kalitta Air, Kalitta Charters, KLM, Korean Air Cargo, Lufthansa, NetJets, Porter, Porter Airlines Canada, Qatar Cargo, SAS, Spirit Airlines, Sun Country Airlines, Swiss, TAP Air Portugal, Turkish Airlines, UPS, Virgin Atlantic, WestJet.
How long does it take to fly from Chicago to Boston?
A direct flight lasts an average of 1h 59m, during which time the aircraft covers a distance of 1366 km.
How much do flights Chicago — Boston cost?
The price of flights Chicago — Boston starts from $34.
What days does the plane fly Chicago — Boston?
Planes fly Chicago — Boston 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun
What airports are there in Chicago and Boston?
In Chicago — Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport. In Boston — Pease Air Force Base, Logan International Airport, Boston City Heliport.
What flights are currently flying from Chicago to Boston?
The following flights fly between Chicago and Boston: WN3787, WN404, WN1427, UA2104, UA2104, AA4106, UA2104, AA4106, WN1915, DL1602, AA4106, AA3821, UA2067, UA2067, UA2067, WN1427, AA3821, WN3786, WN404, WN171, WN3786, AA547, AA1080, AA547, AA547, AA547, B6312, B6312, DL5719, DL5719, UA721, UA721, UA3752, WN3786, B6312, WN5421, AA3821, AA630, AA630, WN1669, DL1371, WN1915, DL2570, DL2570, WN171, B6312, WN2630, UA399, DL2570, DL2570, AA2837, AA2837, AA1271, AA2837, WN1011, UA580, UA580, UA580, UA580, UA580, UA580, UA580, WN3787, DL972, UA580, DL2677, DL2679, UA580, UA2138, UA580, WN3273, AA4766, AA3160, WN3787, AA3160, AA3160, DL2679, DL2677, WN3787, UA1677, UA1677, UA1677, B61012, B61012, B61012, AA1461, AA1461, WN1011, B61012, WN3170, WN3786, WN3170, UA1989, UA1989, WN1933, UA1989, WN3273, WN1132, DL2646, AA3107, B62312, WN937, DL2646, WN1011, AA3107, B62312, AA3107, DL2646, WN1132, WN937, UA1129, UA8229, WN1669, UA2444, WN3786, AA4796, AA4650, AA4404, WN1011, UA1129, AA2682, WN1669, AA2682, AA4650, B62312, UA1495, UA1495, UA1779, UA1779, WN1011
What month is the cheapest to fly from Chicago to Boston?
High season is considered to be November and the cheapest month is July. Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Chicago — Boston flight deals.
Which airlines direct fly from Chicago to Boston?
The following airlines have direct flights Chicago — Boston: Southwest Airlines, United Airlines, American Airlines, Delta Air Lines, JetBlue, Jet Linx Aviation.
Which airlines fly from Chicago to Boston?
All the following airlines flights Chicago — Boston: Aer Lingus, Aeromexico, Air Canada, Air France, Alaska Horizon (Washington State Cougars Livery), Allegiant Air, Amazon Air, American Airlines, Apex Logistics, Austrian Airlines, Avianca, Breeze Airways, British Airways, Cape Air, Cathay Pacific (Oneworld Livery), Copa Airlines, Delta Air Lines, DHL, Emirates, Etihad Airways, FedEx, Frontier (Cubby the Bear Livery), Iberia, Icelandair, ITA Airways, Japan Airlines, Jet Linx Aviation, JetBlue, Kalitta Air, Kalitta Charters, KLM, Korean Air Cargo, Lufthansa, NetJets, Porter, Porter Airlines Canada, Qatar Cargo, SAS, Southwest Airlines, Spirit Airlines, Sun Country Airlines, Swiss, TAP Air Portugal, Turkish Airlines, United Airlines, UPS, Virgin Atlantic, WestJet.