$111 Find Cheap Flights from Boston to Chicago - Compare and Save

These are the earliest and latest flight times available from Boston to Chicago:

• Earliest: departs at 5:39 am and lands at 8:43 am
• Latest: departs at 10:50 pm and lands at 1:54 am.

The flight takes about 3h 04m.

Four cabin classes are available on flights from Boston to Chicago:

• Economy Class
• Premium Economy Class
• Business Class
• First Class

Prices vary by airline.

A nonstop flight from Boston to Chicago takes 3h 04m, covering 850 miles.

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.

Round-trip flights from Boston to Chicago range from $193 to $328, with an average of $250 over the past 12 months. Anything below $193 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 16% above the $250 route average. Book 9 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $157 round-trip via Orlando (MCO), compared to $250 for nonstop.

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 flights are:

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

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

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $35–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Morning is the busiest departure period on Boston to Chicago flights, with 44% of flights leaving in that window. Afternoon departures account for 36%, evening flights for 20%, and night flights for 0%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $213 to $1,150. That means the highest observed fare was about 5x higher than the lowest one.

Three airlines offer in-flight Wi-Fi on Boston to Chicago flights:

• American Airlines
• Delta
• JetBlue

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

One-way fares from Boston to Chicago are currently lower than usual. Average one-way flight prices are about $116, which is 30% below the typical average for this route.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

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

Near Chicago Midway Airport (MDW) — daily rates from around $32:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $28:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Flights from Boston to Chicago usually depart from Boston Logan Intl (BOS) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

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

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 route, 14% of flights were delayed in the past 3 months, with delays averaging 2h 48m.

One-stop flights from Boston to Chicago most commonly connect through:

• Detroit Metropolitan Wayne County (DTW) - 28% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 17% of one-stop connections
• Lambert-St Louis (STL) - 17% of one-stop connections
• New York John F Kennedy Intl (JFK) - 14% of one-stop connections

Yes. Flexible dates can save you up to 14% on flights from Boston to Chicago. Saturday is the cheapest departure day at $233 round-trip on average, while Friday is the most expensive at $268, a difference of $35.

Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

5 airlines operate flights between Boston and Chicago. The airlines offering nonstop flights on this route include:

• American Airlines
• United Airlines
• Southwest
• Delta
• JetBlue

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 17m, compared with 4h 44m via Philadelphia (PHL) and 5h 27m via Baltimore/Washington (BWI).

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

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

Among airlines operating Boston to Chicago 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
• Southwest: offers free seat selection

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

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 always check the fare details before booking.

The MBTA Blue Line provides quick, reliable service to the airport. Travelers can take the Blue Line to the airport station, then board one of the free shuttle buses to all terminal buildings.

Rental car companies are located in the Multi-Modal Facility (MMF). The Airport Transit System (ATS) connects the terminals with the MMF. Hotel and off-airport parking shuttles pick up at the Terminal 2 Arrivals curbside, with some also picking up at Terminal 5.

For most requests, travelers meet their rideshare driver on the Departures level of Terminal 2. There is no parking at the terminal building at any time. The airport provides a cell phone lot for waiting for arriving passengers instead of circling the airport.

Yes, ORD provides Mother's Rooms in every terminal. These rooms offer space for traveling mothers to breastfeed or pump and include a sink, comfortable seats, power outlets and diaper-changing tables. In Terminal 1, a Mother's Room is near Gate B10 on Concourse B. In Terminal 2, they are near Gates E5 and F9. Additional rooms are near Gate L6 in Terminal 3 and near Gates M8, M20, M32 and M37 in Terminal 5. There are also rooms at the Multi-Modal Facility on Level 1, on the North and South Side.

At BOS, elevators have Braille and Emergency Call keys. For travelers with reduced mobility, free Massport Shuttles have low floors for easier boarding, luggage racks and wheelchair lifts. All airlines at BOS also provide wheelchair assistance services.

Yes, pet relief areas are on the arrivals level of every terminal building. Animal relief areas are also available post-security in each terminal.

Boston Logan International Airport (BOS) offers on-site parking in the Central Parking Garage, Economy Garage and Terminal B Garage. The Central Parking Garage is connected to the terminals by covered walkways with moving sidewalks, while the Economy Garage is served by a free shuttle bus from all terminals.