$103 Find Cheap Flights from Boston to Chicago - Compare and Save

The Blue Line Subway is an excellent choice for quick and reliable transportation to the airport. Save the headaches of traffic by taking the MBTA Blue Line to the station at the airport and then simply board one of the free shuttle buses to all of the airport terminal buildings.

The pet relief areas at Boston Logan International Airport (BOS) are located on the arrivals level of every terminal building. In addition, there is a pet relief area located in Terminal E near gate E7. Keep in mind that this is the only pet relief area that is past security.

For most requests, you'll meet your rideshare driver on the Departures level of Terminal 2. As a reminder, there is no parking at the terminal building at any time. It is advisable to use the cell phone lot that is provided at the airport to wait for arriving passengers rather than just circling the airport.

The airport offers a complimentary shuttle to the airport's Multi-Modal Facility, where all on-site car rental companies are located. Travelers can find the shuttle by exiting the Lower Level Baggage Claim and boarding the shuttle bus at the curb front. Each terminal has a designated pickup area outside the building.

Porter Airlines, United Airlines and American Airlines offer some of the most environmental-friendly flights to Chicago from Boston. Their flights emit about 48%, 46% and 42% less carbon respectively than their competitors. Those looking to fly more sustainably from Boston to Chicago should prioritize nonstop flights, embrace the use of recycled plastics and pack light for the trip.

If you’ll be driving to the airport, you’ll be happy to know that Boston Logan International Airport (BOS) offers convenient onsite parking options. Parking is available in Central Parking Garage, Economy Garage, and the Terminal B Garage. All the parking garages are easily accessible from the terminals by the moving sidewalks and walkways. Additionally, the airport partners with other agencies to offer multiple secure offsite parking options.

Boston Logan International Airport (BOS) provides Braille and Emergency Call keys in elevators. All restrooms within the airport are accessible, and it also provides restrooms for the companions. To enhance transit for passengers with reduced mobility, BOS provides Massport Shuttles. These buses are free, are equipped with wheelchair lifts and use visual and audio assistance systems to announce the bus stops. All airlines flying through BOS also run wheelchair assistance services.

Yes, Chicago O’Hare International Airport (ORD) provides Mother's Rooms in every terminal. The rooms offer a space for traveling mothers to breastfeed or pump and are equipped with a sink, comfortable seats, power outlets and diaper changing tables. The rooms are available near Gate B10 on Concourse B in Terminal 1. In Terminal 2, they are by Gates E5 and F9. Others are also near Gate L6 in Terminal 3 and also at Gate M8​, Gate M20​, Gate M32 and Gate M37 in Terminal 5. There are also others at Multi-Modal Facility on Level 1, North and South Side.

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.

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

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

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).

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 travelers should check the fare details before booking.

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

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

Prices vary by airline.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $180 round-trip via New York John F Kennedy Intl (JFK), compared to $237 for nonstop.

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.

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

• Detroit Metropolitan Wayne County (DTW) - 24% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 14% of one-stop connections
• Lambert-St Louis (STL) - 14% of one-stop connections
• Orlando (MCO) - 12% of one-stop connections

Detroit Metropolitan Wayne County (DTW) handles the largest share of one-stop connections on this route.

On the Boston to Chicago route, being flexible with your departure day can save you up to 13%. Saturday is the cheapest day at $221 round-trip on average, while Friday is the most expensive at $253: a $32 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

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, 15% of flights were delayed in the past 3 months, with delays averaging 2 hours 47 minutes.

Morning is the busiest departure period on Boston to Chicago flights, with 44% of flights leaving in that window. Afternoon departures account for 30%, evening flights for 26%, and night flights for 0%.

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

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

• Earliest: departs at 5:41 am and lands at 8:40 am
• Latest: departs at 10:50 pm and lands at 1:49 am.

The flight takes about 2h 59m.

Last-minute fares on this route - booked within 2 weeks of departure - run 17% above the route average of $237. Book 4 weeks before departure for the lowest fares.

A nonstop flight from Boston to Chicago takes 2h 59m, 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.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $185 to $1,156. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Boston to Chicago are currently lower than usual. Average one-way flight prices are about $107, which is 34% 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 flights are:

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

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

Morning 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 at 4h 18m, compared with 4h 44m via Philadelphia (PHL) and 5h 55m via Lambert-St Louis (STL).

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

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
· Dollar
· Ace

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 $30:

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

Round-trip flights from Boston to Chicago range from $181 to $318, with an average of $237 over the past 12 months. Anything below $181 counts as a good deal.

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

• • American Airlines
• • Delta
• • JetBlue