One Way

Popular Filters

+ 1 more

Arrival Airports

One Way Price

USD 187 USD 500

Duration

2 h 5 m 7 h 30 m

Stops From Chicago

Departure From Chicago

6 AM - 12 PM

USD 188

12 PM - 6 PM

USD 231

After 6 PM

USD 232

Arrival at Boston

Before 6 AM

USD 232

6 AM - 12 PM

USD 198

12 PM - 6 PM

USD 188

After 6 PM

USD 231

Alliances & Airlines

Oneworld

(2)

SkyTeam

(4)

Star Alliance

(4)

Layover Airports

Layover Duration

1 h 41 m 3 h 30 m

Top Flights From Chicago

Chicago (CHI) to Boston (BOS) Cheap Flights

Book Chicago to Boston cheap flight tickets โœˆ at lowest price. Get best deals on your upcoming Chicago (CHI)to Boston (BOS) flights only on MakeMyTrip. Also Book Boston to Chicago Cheap Flights. Currently 18 flights flying from Chicago to Boston. To save maximum on flight booking click on below Fare Calendar button and choose your dates.

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Price last updated at 18 Jun 2026 20:51:36
JetBlue Airways

USD 195

USD 188

Chicago to Boston , 25 Jun

JetBlue Airways B6 | 312

10:56

Thu, 25 Jun 26

Terminal T2

Chicago, United States

02 h 26 m

14:22

Thu, 25 Jun 26

Terminal C

Boston, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines

USD 198

Chicago to Boston , 25 Jun

Delta Air Lines DL | 2828

07:10

Thu, 25 Jun 26

Terminal T5

Chicago, United States

02 h 36 m

10:46

Thu, 25 Jun 26

Terminal A

Boston, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines

USD 202

Chicago-Midway to Boston , 25 Jun

Delta Air Lines DL | 1285

06:00

Thu, 25 Jun 26

Chicago-Midway, United States

01 h 55 m

08:55

Thu, 25 Jun 26

Terminal S

Atlanta, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines DL | 862

11:05

Thu, 25 Jun 26

Terminal S

Atlanta, United States

02 h 40 m

13:45

Thu, 25 Jun 26

Terminal A

Boston, United States

BAGGAGE : CHECK INCABIN

Information not available

United Airlines

More Timing Options

USD 241

USD 232

Chicago to Boston , 25 Jun

United Airlines UA | 1186

06:05

Thu, 25 Jun 26

Terminal T1

Chicago, United States

02 h 24 m

09:29

Thu, 25 Jun 26

Terminal B

Boston, United States

BAGGAGE : CHECK INCABIN

Information not available

American Airlines

USD 280

USD 269

Chicago to Boston , 25 Jun

American Airlines AA | 2968

07:00

Thu, 25 Jun 26

Terminal T3

Chicago, United States

02 h 26 m

10:26

Thu, 25 Jun 26

Terminal B

Boston, United States

BAGGAGE : CHECK INCABIN

Information not available

Southwest Airlines

USD 357

Chicago-Midway to Manchester , 25 Jun

Southwest Airlines WN | 830

07:40

Thu, 25 Jun 26

Chicago-Midway, United States

02 h 10 m

10:50

Thu, 25 Jun 26

Manchester, United States

BAGGAGE : CHECK INCABIN

Information not available

Southwest Airlines

More Timing Options

USD 494

Chicago-Midway to Boston , 25 Jun

Southwest Airlines WN | 4611

07:40

Thu, 25 Jun 26

Chicago-Midway, United States

02 h 15 m

10:55

Thu, 25 Jun 26

Terminal B

Boston, United States

BAGGAGE : CHECK INCABIN

Information not available

Chicago to Boston Flights Information:-

Looking for Chicago to Boston Flight? Hereโ€™s all you need to know! For convenience and to save time, pick the airport that is closest to your destination. The nearest airport to Boston is General Edward Lawrence Logan Intl and the IATA code for the same is BOS.
Currently, there are 5 airlines operating flights between the two destinations and approximately 18 flights take off from Chicago to Boston every week.

Need information on Chicago to Boston airfare?

The minimum airfare for a Chicago to Boston flight would be 187, which may go up to 494 depending on the route, booking time and availability.
It is recommended that you book a round-trip, since it always works out to be more economical.

Flight Details for Chicago to Boston

If you are looking for Chicago to Boston flights, there is no dearth of options to choose from. Several reputed airlines currently offer both direct and indirect flights between the two destinations. Some of these are American Airlines, Delta Air Lines, JetBlue Airways, Southwest Airlines, United Airlines. Out of these, only 14 airlines operate direct flights. Indirect flights may involve more travel time, but they usually cost lesser than direct flights.

The number of flights operated by each airline is as follows:American Airlines : 2, Delta Air Lines : 2, JetBlue Airways : 2, Southwest Airlines : 2, United Airlines : 2

To board the first Chicago to Boston flight, choose Delta Air Lines, which departs at 06:00 The last flight for this route is United Airlines, departing at 21:41

Boston Airport Information

General Edward Lawrence Logan Intl

About Chicago (CHI)

Chicago, known as the Windy City, is a vibrant metropolis in Illinois, offering an exciting blend of culture, architecture, and entertainment. It boasts iconic landmarks, world-class museums, and a rich history that attracts millions of visitors each year. Whether you're drawn to its towering skyscrapers, picturesque parks, or diverse neighborhoods, Chicago promises a memorable experience for travelers from the United States.

Best Time to Visit

Chicago's weather varies significantly throughout the year. The ideal time to visit is during the spring (April to June) and fall (September to October) when the temperatures are mild, and the city hosts numerous festivals and events. Summer (July to August) is also popular, offering warm weather perfect for outdoor activities and beach visits, though it can be crowded. Winter (December to February) brings cold temperatures and snow, but it transforms the city into a winter wonderland, ideal for those who enjoy winter sports and holiday festivities.

Getting There

Chicago is well-connected to the United States and the world through its two major airports: O'Hare International Airport (ORD) and Midway International Airport (MDW). Both airports offer numerous flights to Chicago, including cheap flights to Chicago from various U.S. cities. United Airlines, American Airlines, and Delta Airlines are among the top carriers providing Chicago flight tickets. Ensure you have a valid ID for domestic flights and a passport for international travel.

Where to Stay

Chicago offers a wide range of accommodations to suit all budgets. For luxury stays, consider the Magnificent Mile area, home to upscale hotels like The Peninsula and Four Seasons. The Loop is ideal for business travelers and those looking to be close to major attractions, with options like the Palmer House Hilton. Budget-conscious travelers can find affordable hotels and hostels in neighborhoods like River North and Lincoln Park.

Must-See Places & Experiences

Chicago is packed with must-see attractions:
โ€ข Millennium Park: Home to the iconic Cloud Gate sculpture (The Bean)
โ€ข Navy Pier: A hub of entertainment with rides, restaurants, and shops
โ€ข Art Institute of Chicago: Renowned for its extensive art collection
โ€ข Willis Tower Skydeck: Offers breathtaking views from the 103rd floor
โ€ข Museum Campus: Includes the Field Museum, Shedd Aquarium, and Adler Planetarium
For a unique experience, explore the city's diverse neighborhoods like Wicker Park and Pilsen, known for their vibrant arts and dining scenes.

Local Transportation

Chicago's public transportation system, operated by the Chicago Transit Authority (CTA), is efficient and affordable. The 'L' trains and buses cover most of the city, making it easy to get around. Taxis and rideshare services like Uber and Lyft are also readily available. For a scenic option, consider taking a water taxi along the Chicago River.

Food & Dining

Chicago is a food lover's paradise, famous for its deep-dish pizza and Chicago-style hot dogs. Must-try dishes include:
โ€ข Deep-dish pizza from Lou Malnati's or Giordano's
โ€ข Chicago-style hot dogs from Portillo's
โ€ข Italian beef sandwiches from Al's Beef
For fine dining, visit Alinea or Girl & The Goat. The city's diverse culinary scene also offers a range of international cuisines, reflecting its multicultural heritage.

Practical Travel Tips

โ€ข Currency: U.S. Dollar (USD)
โ€ข Language: English
โ€ข Safety: Chicago is generally safe for tourists, but it's wise to stay aware of your surroundings and avoid less populated areas at night.
โ€ข Useful Apps: Download the CTA Transit App for public transport info and Yelp for restaurant reviews.
Start planning your trip and explore the best of Chicago with cheap flight tickets to Chicago available on various travel websites. Enjoy your visit to this dynamic city!

Chicago Address

About Boston (BOS)

Boston is the most famous and largest city in New England, the capital of the state of Massachusetts. The city is one of the most influential, wealthy and historic cities in the United States of America. Its plethora of highly famous museums, attractive historical sites and wealth of live performances, all demonstrate why the city gets over a 16.3 million visitors every year. This makes it one of the ten most famous tourist destinations in the country. The historic โ€˜City of Bostonโ€™ has some of the most fascinating and attractive monuments and tourist attractions in the North-eastern United States. Being rich in traditions makes it a famous tourist location that offers an astonishing dining and sightseeing. Its old town trolley tours offer the most famous sightseeing experience in the city. Some of the major attractions of Boston include Boston Children's Museum, Museum of Fine Arts, Harvard Art Museum, Isabella Stewart Gardner Museum, New England Aquarium, and Semitic Museum and so on. Excellent seafood of Boston is available at the nearby New England coast. Boston has a thriving night-life for all those who are more into night parties and also make it perfect location for having fun with friends. It is known to be a 'drinking' town and bar hopping is extremely easy and commonly done here. Local specialities of the city include baked beans, cod, and clam chowder, so don't forget to taste it. Boston Public Library, Newbury Street, The Christian Science Plaza, Skywalk Observatory, Mary Baker Eddy Library, Boston City Hall, Bunker Hill Monument, Neptune Oyster, Boston Duck Tours and so on are some of the major sightseeing of Boston. You can freely move anywhere in the city as it is well-linked with transport facilities. For air travellers, Boston Logan International Airport is a main gateway to Boston and New England. There are number of leading airlines which provide their regular flight services towards Boston. At MakeMyTrip.com, one can book air ticket online and choose the best deal as per your decided budget. Even you can also do online hotel booking in Boston from MakeMyTrip.com and get huge discounts on it.

Boston Address

Frequently Asked Questions - Chicago to Boston Flights

Can I cancel my ticket from Chicago to Boston without cancellation charges?

To avoid cancellation charges on your air tickets, you need to make a selection at the time of booking for ZERO cancellation. Please note, the zero cancellation facility is chargeable with minimum amount and can help you save a lot at the time sudden cancellations.

Can I find cheap accommodation near to airport when travelling from Chicago to Boston?

There are several accommodation options available near the General Edward Lawrence Logan Intl. You can check for both budget friendly and well as five star accommodation near the airport depending on your requirement and budget. These hotels are mostly suitable for business travellers.

How do MakeMyTrip finds the lowest available dare for flights from Chicago to Boston?

MakeMyTrip is a popular travel portal that also works as a travel search engine that allows you to see best available results for your flight search. Every time you make search for flights to any destination, the MMT algorithm picks all the available air carriers for the route and filter rates basis on the cheapest fare available in their system. At MMT, you can not only search flights on the basis of the fare, but you can also see which flight offers direct route, which has multiple stop-overs, baggage allowance, in-flight meal options, cancellation policy, etc. You can also check available discounts offered by payments partners and air carriers when booking the flight.

Is there a way to make flexible departure date bookings for your Chicago to Boston flight tickets?

Some travel portals like MakeMyTrip offer flexible departure and arrival booking option with certain air carrier when booking from Chicago to Boston. You can check the flexible booking flight options once you get the results filters based on your search and make the booking accordingly. Please note, some airlines make charge extra for flexible travel dates.

Which airlines offer cheapest airfare from Chicago to Boston?

There is no set pricing for airlines to offer cheap flight fare from Chicago to Boston. These fares are mostly decided on the basis of algorithms followed by air carriers to final the prizing based on demand. However, some multiple route flights with stop-overs offer cheap flights as compared to direct flight departing from Chicago to Boston.

What is the best time to book cheap flight tickets from Chicago to Boston?

To get cheap flight tickets from Chicago to Boston, the best time would be to plan your trip during the off season. At that time the flight tickets are usually cheaper than the peak season and the accommodation booking is also available at the affordable price. The other way of booking cheap flight tickets from Chicago (CHI) to Boston (BOS) is to book atleast 4 weeks in advance before your departure date to get competitive pricing on your tickets even during the peak season.

Is passport mandatory to travel from Chicago to Boston?

When making an international trip, passport is mandatory as it defines your identity to the other nation officials. The VISA norms may differ from country to country, which means some would allow Visa on arrival and others may require you to obtain visa in advance. But the availability of passport is mandatory at the time of departure and arrival as well.