BOS - ORD

₹ 11,772 Find Cheap Flights from Boston to Chicago – Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest return flight
₹ 23,448
Typical prices: ₹ 18,252-₹ 29,948
Delta
Tue 16/1Tue 23/1
BOS - ORD • Direct
Cheapest one-way flight
₹ 11,677
Typical prices: ₹ 10,575-₹ 20,476
Frontier
Mon 17/12
BOS - ORD • 1 stop
Advice from real travellers
United Economy Plus adds up to six inches more legroom on this short flight.
United Premier Access includes priority check-in and boarding for a smoother trip.
Expert advice
+1
Expert advice
+1
Direct flights
You can fly direct with American Airlines, United Airlines, and others. Average duration is 3h 09m.
Direct flights
+1
Direct flights
+1
Avoid delays
Most punctual • 91% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 9 weeks in advance save around 22% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 25% price drop
Most popular
Good to know
+1
Good to know
+1
Top stopover airports
Cheapest • Avg ₹ 17,724 (return)
Shortest trip • 4h 39m (one-way)
Insights
Insights
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you enjoy your trip to Chicago O'Hare Intl Airport!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Boston to O'Hare Intl (BOS-ORD)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Boston to O'Hare Intl

Sat, 16 Jan - Sat, 23 Jan
Delta Logo
14:30 - 16:36BOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 06mdirect
Delta Logo
10:18 - 13:45ORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 27mdirect
₹ 23,448Delta
Sat, 21 Nov - Thu, 3 Dec
United Airlines Logo
19:41 - 00:01BOS  Boston Logan Intl-ORD Chicago O'Hare Intl
5h 20m1 stop Washington, D.C. Dulles Intl
United Airlines Logo
10:28 - 13:54ORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 26mdirect
₹ 24,398United Airlines
Thu, 19 Nov - Sun, 22 Nov
United Airlines Logo
07:31 - 09:34BOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 03mdirect
United Airlines Logo
07:00 - 10:19ORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 19mdirect
₹ 25,347United Airlines
Wed, 18 Nov - Tue, 1 Dec
Delta Logo
20:40 - 22:36BOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 56mdirect
Delta Logo
19:45 - 23:17ORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 32mdirect
₹ 25,442Delta
Thu, 19 Nov - Sun, 22 Nov
United Airlines Logo
09:00 - 13:09BOS  Boston Logan Intl-ORD Chicago O'Hare Intl
5h 09m1 stop Newark
United Airlines Logo
13:59 - 17:24ORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 25mdirect
₹ 26,296United Airlines
Thu, 17 Dec - Wed, 23 Dec
United Airlines Logo
09:10 - 11:16BOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 06mdirect
United Airlines Logo
21:49 - 01:18ORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 29mdirect
₹ 26,391United Airlines
Mon, 18 Jan - Wed, 20 Jan
Delta Logo
11:25 - 13:32BOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 07mdirect
Delta Logo
19:25 - 23:06ORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 41mdirect
₹ 26,581Delta
Thu, 10 Dec - Mon, 14 Dec
Delta Logo
12:06 - 19:45BOS  Boston Logan Intl-ORD Chicago O'Hare Intl
8h 39m1 stop Minneapolis St Paul
Delta Logo
10:38 - 14:15ORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 37mdirect
₹ 27,151Delta
Thu, 19 Nov - Sun, 22 Nov
Delta Logo
20:40 - 22:36BOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 56mdirect
Delta Logo
07:05 - 10:32ORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 27mdirect
₹ 27,246Delta
Thu, 19 Nov - Sun, 22 Nov
JetBlue Logo
07:55 - 09:59BOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 04mdirect
JetBlue Logo
17:30 - 20:59ORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 29mdirect
₹ 27,341JetBlue
Booking Insights

Price, demand, and travel trends for Boston to Chicago O'Hare Intl Airport flights

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.

How much is a return flight from Boston to Chicago O'Hare Intl Airport?

Return flights from Boston to Chicago O'Hare Intl Airport typically range from ₹ 18,252 to ₹ 29,948. The lowest price found in the past 5 days was ₹ 23,448 on Delta.

What's the cheapest day of the week to fly from Boston to Chicago O'Hare Intl Airport?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Boston to Chicago O'Hare Intl Airport. It's 8% cheaper than the average day, while Friday is the most expensive, with prices 6% higher.

What is the cheapest month to fly from Boston to Chicago O'Hare Intl Airport?

•January is the cheapest month to fly from Boston to Chicago O'Hare Intl Airport at ₹ 17,563 return.
•October (₹ 26,771) and December (₹ 26,107) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 52% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Boston to Chicago O'Hare Intl Airport the cheapest?

Flights from Boston to Chicago O'Hare Intl Airport are cheapest 9 weeks before departure. Booking in this window typically costs about 22% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for Boston to Chicago O'Hare Intl Airport flights

Low season

February

Cheapest flight

₹ 11,677
Beat the crowds with an average 24% drop in travellers.
The most popular month to fly with an average 25% increase in travellers.
One-way flight from Boston to Chicago O'Hare Intl Airport

When to book flights from Boston to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Boston to O'Hare Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price

Flights from Boston to O'Hare Intl: the best tips from KAYAK users' own experiences

Insights shared by verified travellers who flew the route from Boston to O'Hare Intl 
WeiFlew with United Airlines-Oct 2026
This flight usually departs from gate B28. Enjoy a quick meal at Legal’s or Stephanie’s, refill your water bottle at the water station nearby, and enjoy the very quick boarding process implemented!
GailFlew with JetBlue-Jul 2024
Prepare for a long wait after you actually touch down. Ohare Airport is HUGE and you can taxi for a long time.

Your Boston to Chicago O'Hare Intl Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines, and booking tips.

  • What are the earliest and latest flights from Boston to Chicago O'Hare Intl Airport?

    These are the earliest and latest flight times available from Boston to Chicago O'Hare Intl Airport:

    • Earliest: departs at 05:39 and lands at 08:48
    • Latest: departs at 22:00 and lands at 01:09.

    The flight takes about 3h 09m.

  • Which cabin classes can I book on flights from Boston to Chicago O'Hare Intl Airport?

    Only Economy class is available on flights from Boston to Chicago O'Hare Intl Airport.

  • How long is a flight from Boston to Chicago O'Hare Intl Airport?

    A direct flight from Boston to Chicago O'Hare Intl Airport takes 3h 09m, covering 2,237 km.

  • Do I need a passport to fly from Boston to Chicago O'Hare Intl Airport?

    No, a passport is not required for this domestic route, but you will need another form of identification, such as a driving licence.

  • How much should I expect to pay for a Boston to Chicago O'Hare Intl Airport flight?

    Return flights from Boston to Chicago O'Hare Intl Airport range from ₹ 18,252 to ₹ 29,948, with an average of ₹ 23,471 over the past 12 months. Anything below ₹ 18,252 counts as a good deal.

  • How expensive are last-minute Boston to Chicago O'Hare Intl Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 16% above the ₹ 23,471 route average. Book 9 weeks before departure for the lowest fares.

  • How much can I save by having a stopover when flying from Boston to Chicago O'Hare Intl Airport?

    On this route, stopover flights are cheaper than direct options on average. Stopover fares average ₹ 17,724 return via New York John F Kennedy Intl (JFK), compared with ₹ 23,470 for direct.

  • How does on-time performance compare across airlines flying from Boston to Chicago O'Hare Intl Airport?

    United Airlines is slightly above the route average for timely arrivals, while American Airlines has a lower on-time arrival rate. On-time arrival rates on Boston to Chicago O'Hare Intl Airport flights are:

    • United Airlines: 91% on time
    • American Airlines: 85% on time
    • JetBlue: 85% on time

    On average, flights on this route are punctual 86% of the time.

  • What is the standard checked bag allowance on flights from Boston to Chicago O'Hare Intl Airport?

    There is no standard. Checked bag policies vary by airline on this route. Most carriers charge ₹ 3,323–₹ 9,492 for the first checked bag in Economy. Premium fares and elite status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Boston to Chicago O'Hare Intl Airport?

    The Boeing 737-800 family is used most often on this route, operated mainly by American Airlines and United Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

  • How are flight departures from Boston to Chicago O'Hare Intl Airport spread across the day?

    Morning is the busiest departure period on Boston to Chicago O'Hare Intl Airport flights, with 43% leaving in that window. Afternoon departures account for 38%, Evening flights for 19%, and Night flights for 0%.

  • Have flight prices from Boston to Chicago O'Hare Intl Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, return flight prices on this route showed a wide range, from about ₹ 23,448 to ₹ 84,965. That means the highest observed fare was about 4x higher than the lowest one.

  • Which airlines offer Wi-Fi on Boston to Chicago O'Hare Intl Airport flights?

    Three airlines offer in-flight Wi-Fi on Boston to Chicago O'Hare Intl Airport flights:

    • American Airlines
    • Delta
    • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty programme, while others are paid add-ons priced by flight length.

  • How are flight prices from Boston to Chicago O'Hare Intl Airport looking right now?

    One-way fares from Boston to Chicago O'Hare Intl Airport are currently lower than usual. Average one-way flight prices are about ₹ 13,718, which is 13% below the typical average for this route.

  • Which car hire options are available at Chicago O'Hare Intl Airport (ORD)?

    Chicago O'Hare Intl Airport (ORD) hosts 5 major car rental companies, with daily rates starting from around ₹ 6,032 for economy cars. Top options include:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

  • Which airports can I use when flying from Boston to Chicago O'Hare Intl Airport?

    Flights from Boston to Chicago O'Hare Intl Airport usually depart from Boston Logan Intl (BOS) and arrive at Chicago O'Hare Intl (ORD).

  • What time of day has the fewest delays on flights from Boston to Chicago O'Hare Intl Airport?

    Morning flights have the fewest delays on this route, while evening departures tend to have the most.

  • At what point is a flight considered delayed from Boston to Chicago O'Hare Intl Airport?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Boston to Chicago O'Hare Intl Airport route, 14% of flights were delayed in the past three months, with delays averaging 2h 48m.

  • Which airports do connecting flights from Boston to Chicago O'Hare Intl Airport pass through?

    One-stop flights from Boston to Chicago O'Hare Intl Airport most commonly connect through:

    • New York John F Kennedy Intl (JFK) – 50% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) – 20% of one-stop connections
    • Nashville Intl (BNA) – 10% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) – 10% of one-stop connections

  • Can I save money by using flexible dates for flights from Boston to Chicago O'Hare Intl Airport?

    Yes. Flexible dates can save you up to 13% on flights from Boston to Chicago O'Hare Intl Airport. Wednesday is the cheapest departure day at ₹ 21,645 return on average, while Friday is the most expensive at ₹ 24,872, a difference of ₹ 3,228.

    KAYAK's flexible dates feature shows options up to three days before and after your selected dates, making it easier to compare nearby fares.

  • Which airlines fly from Boston to Chicago O'Hare Intl Airport?

    4 airlines operate flights between Boston and Chicago O'Hare Intl Airport. The airlines offering direct flights on this route include:

    • American Airlines
    • United Airlines
    • Delta
    • JetBlue

  • How much time can I save by choosing a different stopover airport from Boston to Chicago O'Hare Intl Airport?

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time of 4h 39m, compared to 4h 44m via Philadelphia (PHL) and 6h 13m via New York John F Kennedy Intl (JFK).

  • What is the time difference between Boston and Chicago O'Hare Intl Airport?

    Chicago O'Hare Intl Airport is 1 hour behind Boston (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago O'Hare Intl Airport?

    Some of the most popular sights in Chicago O'Hare Intl Airport are River North, Millennium Park, and Magnificent Mile. These are among the most viewed places in Chicago O'Hare Intl Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Boston to Chicago O'Hare Intl Airport flights?

    Among airlines operating Boston to Chicago O'Hare Intl Airport flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Delta: offers extra legroom; offers free seat selection
    • JetBlue: offers extra legroom; offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Boston to Chicago O'Hare Intl Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy class
    • American Airlines: a cabin bag and a checked bag in Economy class
    • Delta: a cabin bag and a checked bag in Economy class

    Baggage allowance can vary by ticket type, cabin class, route, and airline, so always check the fare details before booking.

Your guide to booking Boston to Chicago O'Hare Intl Airport flights

Get tips on when to book, when to fly, and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Friday. On this route, Wednesday flights average ₹ 21,645, which is about ₹ 3,228 less than Friday fares (13% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 9 weeks before you fly. On this route, that window historically saves about 22% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Boston to Chicago O'Hare Intl Airport trip for January. Fares historically average ₹ 17,563 return in that month – typically ₹ 9,208 less than the most expensive month, which is October (based on the last 12 months).
  • For the best chance of arriving on time, fly with United Airlines. Over the past three months, 91% of United Airlines flights from Boston to Chicago O'Hare Intl Airport arrived on time, slightly above the route average of 86%. When flights on this route arrive late, they're delayed by an average of 2h 48m, so choosing an airline with strong on-time performance can make a difference if you're on a tight schedule.
  • If you have the time, taking a 1-stop flight through New York John F Kennedy Intl Airport (JFK) can be cheaper than flying direct. The cheapest stopover option averages ₹ 17,724 return on this route – about ₹ 5,746 less than direct flights (based on the last 12 months).

Prefer to fly direct from Boston Logan Intl to Chicago O'Hare Intl?

 
Find which airlines fly direct from Boston Logan Intl Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

Boston Logan Intl to Chicago O'Hare Intl

Monday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Tuesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Wednesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Thursday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Friday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Saturday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Sunday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

See more direct flights

Direct returns

Chicago O'Hare Intl to Boston Logan Intl

Monday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Tuesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Wednesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Thursday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Friday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Saturday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Sunday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

See more direct flights

More options for your flight from Boston to O'Hare Intl

Complete your trip to Chicago with a hotel stay or car hire