Cheap flights from Boston to Chicago

Logan
BOS
Chicago FSS
CHI

Flight deals from Boston to Chicago

Below you can see the best deals on flights Boston — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 9 September, from $78.

Top 10 cheap flights from Boston to Chicago

F9
F9
$ 95

Boston — Chicago

12:54—17:51
11 Sep 2026
5 h 57 m
1 stop
DL
F9
$ 97

Boston — Chicago

07:30—22:02
12 Sep 2026
15 h 32 m
1 stop
F9
F9
$ 98

Boston — Chicago

12:54—18:23
12 Sep 2026
6 h 29 m
1 stop
F9
F9
$ 101

Boston — Chicago

12:54—23:44
11 Sep 2026
11 h 50 m
1 stop
F9
F9
$ 104

Boston — Chicago

12:45—22:47
6 Sep 2026
11 h 2 m
1 stop
F9
F9
$ 104

Boston — Chicago

12:45—22:47
31 Aug 2026
11 h 2 m
1 stop
F9
F9
$ 104

Boston — Chicago

12:45—22:47
5 Sep 2026
11 h 2 m
1 stop
F9
F9
$ 104

Boston — Chicago

12:54—23:44
10 Sep 2026
11 h 50 m
1 stop
DL
$ 127

Boston — Chicago

13:35—15:26
12 Sep 2026
2 h 51 m
Direct flight
DL
$ 127

Boston — Chicago

07:30—09:24
12 Sep 2026
2 h 54 m
Direct flight

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Boston — Chicago flight

Looking for cheap flights from Boston to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your Boston — Chicago ticket online at the best price.

The route has direct flights — around 394 flights per week, flights are operated by American Airlines, United Airlines, Southwest Airlines, Delta and 8 more airlines, a nonstop flight takes about 2 h 52 min, the distance between the cities is around 1,369 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $63Min. price
NovemberCheapest
JunePeak season
YesDirect flights
1,369 kmDistance
2 h 52 minTravel time
13Airlines
394 / wkFlights

Flight schedule from Boston to Chicago

The table shows direct flights from Boston to Chicago on the selected date. The flight takes approximately 2 h 52 min. Regular flights are operated by American Airlines, United Airlines, Southwest Airlines and Delta. Departures from Logan International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 14 Aug 2026

Flight ticket prices by day: Boston — Chicago

Below is a calendar of the lowest flight ticket prices for Boston — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $63 in November, and the most expensive are around $132 in June. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Average one-way fares from Boston to Chicago by month. Tickets are usually cheapest in September (around $100) and priciest in July (about $145) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$103lowMay$106lowSep$100low
Feb$103lowJun$139highOct$105low
Mar$115mediumJul$145highNov$118medium
Apr$115mediumAug$139highDec$143high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in November and most expensive in June. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a Boston — Chicago ticket

  • Book ahead: fares for Boston — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • The cheapest month to fly to Chicago is usually November — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Boston — Chicago route are operated by 12 airlines; American Airlines runs the most flights (around 34% of all flights). Compare carriers, flight shares and schedules below.

  • American AirlinesAA
    45x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight BOS → ORD45x/week
      Duration
      3h 8m
      Days
      MTWTFSS
    34.0%Open →
  • United AirlinesUA
    41x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight BOS → ORD41x/week
      Duration
      2h 56m
      Days
      MTWTFSS
    31.0%Open →
  • Southwest AirlinesWN
    13x/week
    WebsiteFleet: 817140M pax/year
    • Direct flight BOS → MDW13x/week
      Duration
      2h 35m
      Days
      MTWTFSS
    9.6%Open →
  • DeltaDL
    12x/week
    WebsiteFleet: 986190M pax/year
    • Direct flight BOS → ORD12x/week
      Duration
      2h 46m
      Days
      MTWTFSS
    9.4%Open →
  • JetBlueB6
    9x/week
    WebsiteFleet: 30742.5M pax/year
    • Direct flight BOS → ORD9x/week
      Duration
      3h
      Days
      MTWTFSS
    6.6%Open →
  • Japan AirlinesJL
    3x/week
    WebsiteFleet: 14540M pax/year
    • Direct flight BOS → ORD3x/week
    2.5%Open →
  • IberiaIB
    3x/week
    WebsiteFleet: 9224M pax/year
    • Direct flight BOS → ORD3x/week
    2.3%Open →
  • British AirwaysBA
    3x/week
    WebsiteFleet: 29243M pax/year
    • Direct flight BOS → ORD3x/week
      Duration
      2h 58m
      Days
      MTWTFSS
    2.0%Open →
  • Alaska AirlinesAS
    2x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight BOS → ORD2x/week
    1.3%Open →
  • Virgin AtlanticVS
    1x/week
    WebsiteFleet: 415.3M pax/year
    • Direct flight BOS → ORD1x/week
    0.5%Open →
  • SASSK
    1x/week
    WebsiteFleet: 13524M pax/year
    • Direct flight BOS → ORD1x/week
    0.3%Open →
  • Latam Airlines GroupLA
    1x/week
    WebsiteFleet: 34782M pax/year
    • Direct flight BOS → ORD1x/week
    0.3%Open →

Cities and airports on the Boston — Chicago route

Flights Boston — Chicago depart from Logan International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Boston

BOS
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Boston — Chicago flight

How long is the flight from Boston to Chicago?

A nonstop Boston — Chicago flight takes about 2 h 52 min — the distance between the cities is around 1,369 km.

How far is it from Boston to Chicago?

The distance from Boston to Chicago is about 1,369 km, which a nonstop flight covers in around 2 h 52 min.

Are there direct flights from Boston to Chicago?

Yes, there are nonstop flights Boston — Chicago — around 394 flights per week.

Which airlines fly from Boston to Chicago?

Airlines operating Boston — Chicago include American Airlines, United Airlines, Southwest Airlines, Delta, JetBlue. See the full list with schedules in the "Airlines" section on this page.

Which airports do Boston — Chicago flights use?

Flights from Boston depart from Logan International Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Boston to Chicago?

The price of a Boston — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in November, and most expensive in June. Tickets typically cost between $63 and $132. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Boston — Chicago?

Flights Boston — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is November. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Boston to Chicago?

To catch a low fare Boston — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually November.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Boston

See all
New York CityWashington, D.C.TorontoSan FranciscoAtlantaSeattleLos AngelesPhiladelphiaNantucketLondonDallasOrlandoDenverFort LauderdaleDetroitCharlotteRaleighMontrealNashvilleMarthas VineyardMiamiMinneapolisBuffaloSan DiegoPhoenixMadridTampaPittsburghClevelandBarcelonaIndianapolisSan JuanDublinHoustonParisLas VegasAustinRichmondCincinnatiAmsterdam

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleDallasHoustonOrlandoDenverLondonNashvilleIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochesterCleveland

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