We use marketing and analytics cookies.
Click "Accept" if thata's okay with you.

Find Cheap Flights from Chicago to Boston (CHI to BOS)

From where?
Show more
Show more
  • Please enter origin city or airport.
  • Please enter destination city or airport.
  • Please enter valid from city or airport code.
  • Please enter valid to city or airport code.
  • Please enter depart date.
  • Please enter depart date.
  • Please enter return date.
  • Please select number of passengers.
Chicago
- Boston
×
Traveler / Coach Class
  • originquery:
  • destquery:
  • originCityCode:
  • originLocation:
  • originCity:
  • destCity:
  • totalPax:
  • roomCount:
  • adultCount:
  • seniorCount:
  • childrenCount:
  • roomOneAd:
  • roomOneSr:
  • roomOneCh:
  • roomTwoAd:
  • roomTwoSr:
  • roomTwoCh:
  • roomThreeAd:
  • roomThreeSr:
  • roomThreeCh:
  • showOrDropdown:
  • cabinClass:
  • Please enter origin city or airport.
  • Please enter destination city or airport.
  • Please enter valid from city or airport code.
  • Please enter valid to city or airport code.
  • Select check-in date.
  • Select check-out date.
  Enter airport or city
  Enter airport or city
×
1 Room, Travelers
From where?
Show more
Show more
  • originquery:
  • originCityCode:
  • originLocation:
  • originCity:
  • destquery:
  • destCityCode:
  • destLocation:
  • destCity:
  • dropoffLocation:
  • adultCount:
  • childrenCount:
  • roomCount:
  • roomOneAd:
  • roomOneCh:
  • roomTwoAd:
  • roomTwoCh:
  • roomThreeAd:
  • roomThreeCh:
Where are you going?
Show more
  • Please enter City/Airport/Landmark.
  • Please enter a valid City/Airport/Landmark.
  • Pick-Up Location can not be left blank!
  • Please enter a valid Pick-Up Location.
  • Select check-in date.
  • Select check-out date.
  • Select pick-up & drop-off date.
  Enter Destination
×
1 Room, Traveler
Choose your drop-off location
Show more
  Pick-up Location
×
Where do you want to stay?
Show more
  • Please enter City/Airport/Landmark.
  • Please enter a valid City/Airport/Landmark.
  • Select check-in date.
  • Select check-out date.
  City, Airport or Landmark
×
1 Room, Traveler
Choose your pick-up location
Show more
Choose your drop-off location
Show more
  • Please enter origin city or airport.
  • Please enter destination city or airport.
  • Please enter valid from city or airport code.
  • Please enter valid to city or airport code.
  • Please enter depart date.
  • Please enter return date.
  Pick-up City / Airport / Zip
×
Need help booking? Our agents are ready!Choose from over 500 airlines.Call us 24/7 at 1-845-848-0154
Hawaiian AirlinesHawaiian Airlines
JetBlue AirwaysJetBlue Airways
Turkish AirlinesTurkish Airlines
Call us
Here’s why travelers choose CheapOair

Get Great Deals!

Choose from 500+ airlines for low airfares!

Price Match Promise

Find low prices to destinations worldwide.

Easy Cancellations with CheapOair

Convenient self-service options available online.

Expert Guidance

Get personalized assistance from our travel experts.

Chicago to Boston Flight Deals

 

* All fares above were last found on:  .Fares are round trip. Fares incl. all fuel surcharges, taxes & fees and our service fees. Displayed fares are based on historical data, are subject to change and cannot be guaranteed at the time of booking. See all booking terms and conditions

Cheap Flights from Chicago to Boston

Grab cheap flights from Chicago to Boston

Things to know before you book your flights from Chicago to Boston

Currency: The US Dollar (USD) is used in Boston and all of USA.

Language: English is the primary language spoken in Boston. However, owing to its sizeable Latino populace, Spanish is also widely spoken here.

Local Transport: The city is served by the subways, trolleys, buses, taxis, and ride-sharing services. A ferry service connects Long Wharf with Boston Navy Yard.

Explore Boston

Capital of Massachusetts, Boston was founded in 1630. The city is among the oldest cities in the United States of America. Boston is famed for its significant role in the American Revolution. The city was the site of several historic events, namely, Battle of Bunker Hill, Boston Massacre, Boston Tea Party, and Siege of Boston. Today, the city is an international center of business, innovation, entrepreneurship, education, and medicine. Boston is lined with diverse neighborhoods, Downtown is home to city’s most popular attractions such as the Freedom Trail and the North End is the hub of Italian-American community. Do not forget to indulge in local food and spot some of the city’s oldest buildings while you explore these neighborhoods.

A culturally rich city, Boston hosts several annual events around the year. Few of the major festivals and events held in Boston are Boston Wine Expo (February), St. Patrick's Day (March), Boston Marathon (April), Boston Early Music Festival (June), Boston Pride Parade (June), Boston Harborfest (July), Salem Jazz and Soul Festival (August), Boston Arts Festival (September), Boston Book Festival (October), Halloween (October), and Festival of the Dead (October). Visitors can book Chicago to Boston flight tickets keeping in mind such prominent events.

Major attractions in Boston

  • Freedom Trail
  • Beacon Hill
  • Museum of Fine Arts Boston
  • Faneuil Hall Marketplace
  • John F. Kennedy Presidential Library and Museum
  • New England Aquarium
  • Boston Common
  • Skywalk Observatory
  • Boston Harborwalk
  • Boston Tea Party Ships & Museum

When to visit Boston

The best time to visit Boston is from May to October during late spring and early fall season when the weather is pleasant for sightseeing. Many travelers wish to visit Boston in October to celebrate Halloween in Salem. Airfares tend to peak in October, hence, it is advised to book flights in advance to score Chicago to Boston flight deals.

Share your Travel experience

Once you’re done sharing photos from your trip to Boston, do not forget to share your Boston experience with us through the CheapOair review section. Help and inspire other travelers by sharing your valuable opinion. Remember, your reviews can help us make our service better.

CheapOair Customer Reviews

Eugene OR

My trip was planned perfectly, from flight to accommodations. I'll be visiting again in the Spring and using CheapOair to plan again. Very satisfied! - Steven  Dec 12, 2024

Greece Getaway

My first experience with CheapOair was very good! The reservations made to fly to Greece had smooth connections at each airport. I was hoping for the ability to watch the reservation price and adjust it as the trip got closer, but once I locked in my reservation, the price couldn’t be changed. Text messages from them were clear and kept me informed on the flight plan! I would rate this experience as very good. - Bette  Dec 01, 2024

x