₹ 11,288 Find Cheap Flights from Boston to Chicago – Compare and Save

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.

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

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

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

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

Two cabin classes are available on flights from Boston to Chicago O'Hare Intl Airport:

• Economy class
• First Class

On this route, stopover flights are cheaper than direct options on average. Stopover fares average ₹ 17,861 return via New York John F Kennedy Intl (JFK), compared with ₹ 22,473 for direct.

There is no standard. Checked bag policies vary by airline on this route. Most carriers charge ₹ 3,348–₹ 9,566 for the first checked bag in Economy. Premium fares and elite status bookings typically include a free checked bag.

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 9 variants.

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

• New York John F Kennedy Intl (JFK) – 31% of one-stop connections
• Nashville Intl (BNA) – 19% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) – 13% of one-stop connections
• Baltimore/Washington (BWI) – 6% of one-stop connections

New York John F Kennedy Intl (JFK) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 13% on the Boston to Chicago O'Hare Intl Airport route. Wednesday is the cheapest departure day at ₹ 20,855 return on average, while Friday is the most expensive at ₹ 23,725, a difference of ₹ 2,870. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

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, 15% of flights were delayed in the past 3 months, with delays averaging 2 hours 48 minutes.

Morning is the busiest departure period on Boston to Chicago O'Hare Intl Airport flights, with 42% leaving in that window. Afternoon departures account for 33%, Evening flights for 25%, and Night flights for 0%.

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

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 08:43
• Latest: departs at 22:00 and lands at 01:04.

The flight takes about 3h 04m.

Last-minute fares on this route (booked within 2 weeks of departure) run 17% above the route average of ₹ 22,452. Book 4 weeks before departure for the lowest fares.

A direct flight from Boston to Chicago O'Hare Intl Airport takes 3h 04m, covering 2,237 km.

No. A passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, return flight prices on this route showed a wide range, from about ₹ 20,759 to ₹ 110,684. That means the highest observed fare was about 5x higher than the lowest one.

One-way fares from Boston to Chicago O'Hare Intl Airport are currently lower than usual. Average one-way flight prices are about ₹ 12,207, which is 21% below the typical average for this route.

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

• United Airlines: 90% on time
• JetBlue: 85% on time
• American Airlines: 84% on time

On average, flights on this route are punctual 85% of the time.

Night flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

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).

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.

Chicago O'Hare Intl Airport (ORD) hosts 5 major car hire companies, with daily rates starting from around ₹ 1,627 for economy cars. Top options include:
• Routes Car & Truck Rentals
• Europcar
• Hertz
• Dollar
• Ace

Return flights from Boston to Chicago O'Hare Intl Airport range from ₹ 17,286 to ₹ 29,435, with an average of ₹ 22,452 over the past 12 months. Anything below ₹ 17,286 counts as a good deal.

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.