Cheap flights from Chicago to Boston

Chicago FSS
CHI
Logan
BOS

Flight deals from Chicago to Boston

Below you can see the best deals on flights Chicago — Boston 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 7 October, from $92.

Top 10 cheap flights from Chicago to Boston

UA
$ 102

Chicago — Boston

06:10—09:33
9 Sep 2026
2 h 23 m
Direct flight
UA
$ 102

Chicago — Boston

21:40—01:10
9 Sep 2026
2 h 30 m
Direct flight
UA
$ 102

Chicago — Boston

07:30—11:01
9 Sep 2026
2 h 31 m
Direct flight
UA
$ 102

Chicago — Boston

12:52—16:27
9 Sep 2026
2 h 35 m
Direct flight
UA
$ 102

Chicago — Boston

18:24—21:59
9 Sep 2026
2 h 35 m
Direct flight
UA
$ 102

Chicago — Boston

19:55—23:30
9 Sep 2026
2 h 35 m
Direct flight
UA
$ 102

Chicago — Boston

13:55—17:36
9 Sep 2026
2 h 41 m
Direct flight
UA
$ 102

Chicago — Boston

10:25—14:07
9 Sep 2026
2 h 42 m
Direct flight
UA
$ 102

Chicago — Boston

09:07—12:50
9 Sep 2026
2 h 43 m
Direct flight
UA
$ 102

Chicago — Boston

15:35—19:19
9 Sep 2026
2 h 44 m
Direct flight

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

About the Chicago — Boston flight

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

The route has direct flights — around 391 flights per week, flights are operated by American Airlines, United Airlines, Southwest Airlines, Delta and 7 more airlines, a nonstop flight takes about 2 h 24 min, the distance between the cities is around 1,369 km.

Planning your trip? You may find our Boston travel guide, how to get from the airport into town and Boston 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 $79Min. price
NovemberCheapest
MayPeak season
YesDirect flights
1,369 kmDistance
2 h 24 minTravel time
11Airlines
391 / wkFlights

Flight schedule from Chicago to Boston

The table shows direct flights from Chicago to Boston on the selected date. The flight takes approximately 2 h 24 min. Regular flights are operated by American Airlines, United Airlines, Southwest Airlines and Delta. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Logan 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: Chicago — Boston

Below is a calendar of the lowest flight ticket prices for Chicago — Boston by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $79 in November, and the most expensive are around $133 in May. 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 Chicago to Boston by month. Tickets are usually cheapest in January (around $126) and priciest in August (about $173) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$126lowMay$144mediumSep$132low
Feb$132lowJun$149mediumOct$131low
Mar$150highJul$161highNov$138medium
Apr$155highAug$173highDec$161high

Some values are estimated based on seasonality.

When to fly

Weather in Boston: it is warmest in July (up to 28 °C on average) and coolest in January (around 3 °C). The driest month is September.

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

Temperature · Boston

Dry and wet days · Boston

Wind speed and direction · Boston

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

  • Book ahead: fares for Chicago — Boston 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.
  • Chicago is served by more than one airport — compare fares and travel time to each before you book.
  • The cheapest month to fly to Boston 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 Chicago — Boston route are operated by 11 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 ORD → BOS45x/week
      Duration
      2h 33m
      Days
      MTWTFSS
    34.3%Open →
  • United AirlinesUA
    37x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → BOS37x/week
      Duration
      2h 35m
      Days
      MTWTFSS
    28.4%Open →
  • Southwest AirlinesWN
    13x/week
    WebsiteFleet: 817140M pax/year
    • Direct flight MDW → BOS13x/week
      Duration
      2h 21m
      Days
      MTWTFSS
    9.7%Open →
  • DeltaDL
    11x/week
    WebsiteFleet: 986190M pax/year
    • Direct flight ORD → BOS11x/week
      Duration
      2h 29m
      Days
      MTWTFSS
    8.7%Open →
  • JetBlueB6
    9x/week
    WebsiteFleet: 30742.5M pax/year
    • Direct flight ORD → BOS9x/week
      Duration
      2h 27m
      Days
      MTWTFSS
    6.6%Open →
  • Alaska AirlinesAS
    8x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight ORD → BOS8x/week
    6.1%Open →
  • British AirwaysBA
    4x/week
    WebsiteFleet: 29243M pax/year
    • Direct flight ORD → BOS4x/week
    3.3%Open →
  • Virgin AtlanticVS
    1x/week
    WebsiteFleet: 415.3M pax/year
    • Direct flight ORD → BOS1x/week
      Duration
      2h 1m
      Days
      MTWTFSS
    1.0%Open →
  • WestJetWS
    1x/week
    WebsiteFleet: 15325M pax/year
    • Direct flight ORD → BOS1x/week
    0.8%Open →
  • Japan AirlinesJL
    1x/week
    WebsiteFleet: 14540M pax/year
    • Direct flight ORD → BOS1x/week
    0.5%Open →
  • IberiaIB
    1x/week
    WebsiteFleet: 9224M pax/year
    • Direct flight ORD → BOS1x/week
    0.5%Open →

Cities and airports on the Chicago — Boston route

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

Departure

Chicago

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

Boston

BOS
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 Chicago — Boston flight

How long is the flight from Chicago to Boston?

A nonstop Chicago — Boston flight takes about 2 h 24 min — the distance between the cities is around 1,369 km.

How far is it from Chicago to Boston?

The distance from Chicago to Boston is about 1,369 km, which a nonstop flight covers in around 2 h 24 min.

Are there direct flights from Chicago to Boston?

Yes, there are nonstop flights Chicago — Boston — around 391 flights per week.

Which airlines fly from Chicago to Boston?

Airlines operating Chicago — Boston 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 Chicago — Boston flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Logan 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 Chicago to Boston?

The price of a Chicago — Boston ticket depends on your travel date, season and demand: it is usually cheapest to fly in November, and most expensive in May. Tickets typically cost between $79 and $133. Check the current lowest fare and low-price calendar on this page.

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

Flights Chicago — Boston 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 Chicago to Boston?

To catch a low fare Chicago — Boston, 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 Chicago

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

Where else you can fly from Boston

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

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