$108 Find Cheap Flights from Chicago to Boston - Compare and Save

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

• Earliest: departs at 5:30 am and lands at 7:59 am
• Latest: departs at 9:49 pm and lands at 12:18 am.

The flight takes about 2h 29m.

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

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

Prices vary by airline.

A nonstop flight from Chicago to Boston takes 2h 29m, 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 Chicago to Boston range from $189 to $324, with an average of $245 over the past 12 months. Anything below $189 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 19% above the $245 route average. Book 25 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $201 round-trip via New York John F Kennedy Intl (JFK), compared to $244 for nonstop.

Delta is slightly above the route average for timely arrivals, while JetBlue has a lower on-time arrival rate. On-time arrival rates on Chicago to Boston flights are:

• Delta: 79% on time
• JetBlue: 75% on time
• United Airlines: 74% on time

Overall, flights on this route are punctual 74% 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 Chicago to Boston flights, with 36% of flights leaving in that window. Afternoon departures account for 32%, evening flights for 28%, and night flights for 4%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $222 to $1,080. That means the highest observed fare was about 5x higher than the lowest one.

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

• American Airlines
• JetBlue
• Delta

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 Chicago to Boston are currently lower than usual. Average one-way flight prices are about $121, which is 29% below the typical average for this route.

Boston Logan Intl Airport (BOS) hosts 5 major car rental companies, with daily rates averaging $77 for economy cars. Top options include:

• Dollar
• Hertz
• Budget
• Thrifty
• Sixt

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

Morning flights have the fewest delays on this route, while afternoon 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 Chicago to Boston route, 26% of flights were delayed in the past 3 months, with delays averaging 2h 38m.

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

• Chicago O'Hare Intl (ORD) - 59% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 10% of one-stop connections
• New York John F Kennedy Intl (JFK) - 7% of one-stop connections
• Philadelphia (PHL) - 7% of one-stop connections

Yes. Flexible dates can save you up to 22% on flights from Chicago to Boston. Wednesday is the cheapest departure day at $225 round-trip on average, while Monday is the most expensive at $285, a difference of $60.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

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

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

Flying via Lambert-St Louis (STL) gives the shortest average 1-stop total travel time at 4h 51m, compared with 5h 05m via Washington, D.C. Reagan-National (DCA) and 5h 25m via Indianapolis (IND).

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

Some of the most popular sights in Boston are TD Garden, Fenway Park and Boston Common. These are among the most viewed places in Boston on KAYAK.

Among airlines operating Chicago to Boston flights:

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

• American Airlines: a cabin bag and a checked bag in Economy Class
• United Airlines: a cabin bag and a checked bag in Economy Class
• JetBlue: 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.

If you are traveling with a pet or service animal, make sure to stop by one of the pet relief areas in Logan International Airport after your flight has landed. There is a designated area conveniently located outside of the Arrivals doors for every terminal, and complimentary waste bags are provided for pet owners.

The Hilton Boston Logan Airport is a chic, 4-star hotel that is directly connected to Logan International Airport via a skybridge and is less than a 7-minute drive from the Boston Common Park. The Hyatt Regency Boston Harbor is a standard option that is only a mile from the airport and a 5-minute drive from the famous Faneuil Hall.

The Go Go White Sox Bar and Grill is located in the Central Market of Chicago Midway International Airport and serves classic American meals, while the Midway Pour House is in Concourse A and is known for having a variety of craft beers. Dunkin’ Donuts and Cafe Espresso are good options for travelers with little time that would like to purchase some to-go items.

Logan International Airport has the Our Lady of the Airways Chapel that is located in Terminal C of the Arrivals level. It is open during standard business hours and is available to all travelers, no matter what their spiritual affiliation is.

The distance between the Freedom Trail and Boston Logan International Airport (BOS) is around 3.7 miles, and various transportation options run between the two points. Line 88 bus and the subway provide the best opportunity to travel between the two points, taking about 26min to cover the distance. However, a taxi is a quicker option, taking about 6min to get there.

Travelers arriving in BOS from Chicago while weary can seek some therapy in one of the spas on this property. XpresSpa at Terminal B provides ideal services to help you relax and self-indulge. They include manicures, pedicures, facials, and deep-tissue massages.

If your wallet is depleted and you want to recharge it, you’ll find several ATMs at BOS run by numerous banks and credit unions. These ATMs are located throughout the airport terminals, pre-and post-security. For instance, Bank of America has its ATMs at the Arrivals Level, East End by Taxi Stand, Pre-Security.

BOS caters to the needs of moms and the littlest family members through the provision of Mamava suites where lactating mothers can pump and breastfeed in privacy. You can locate one of them in Terminal E post-security in the Women's Restroom lobby.