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

Last minute flights from Chicago to Boston

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Prices shown below were available within the past 3 days for the period specified and should not be considered the final price offered. Please note that availability and prices are subject to change.

Chicago Boston

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Sat, 11 Jan ORD - BOS

Wed, 15 Jan BOS - ORD

$151 $145

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Chicago Boston

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Mon, 06 Jan ORD - BOS

$39 $37

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Chicago Boston

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Fri, 03 Jan ORD - BOS

Mon, 06 Jan BOS - ORD

$107 $104

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Chicago Boston

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Wed, 25 Dec ORD - BOS

Fri, 03 Jan BOS - ORD

$214 $210

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Chicago Boston

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Fri, 10 Jan ORD - BOS

Mon, 13 Jan BOS - ORD

$137 $131

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Chicago Boston

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Tue, 14 Jan ORD - BOS

Sat, 18 Jan BOS - ORD

$129 $126

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Route information

Distance: 854 miles

Chicago airports

O'hare International Airport (ORD) How far from city center: 14 miles

Midway Airport (MDW) How far from city center: 4 miles

Boston airports

Logan International Airport (BOS) How far from city center: 3 miles

Are you searching for flights from Chicago to Boston?

Travel from Boston Logan International Airport (BOS) to Chicago O'hare International Airport (ORD)

On average, there are 80 direct flights a day between Boston (BOS) and Chicago (ORD) airports. Several airlines are offering this route, amongst them: United Airlines, American Airlines, Delta, Frontier Airlines, Southwest Airlines, Spirit Airlines. The duration of a direct flight between Boston, Massachusetts and Chicago, Illinois is on average 2 hours and a half. The return tickets’ price is about $80. The price varies depending on the season, the day of the week, the flights’ hours, the class (economy, business) and the airline.

Going from Downtown Boston to Logan International Airport (BOS)

Logan International Airport (BOS) is 3 miles away from Downtown Boston. Whether you choose to rent a car, take a cab or public transportation, you will reach the airport quickly. Public transportation is, obviously, the cheapest option. You can either take the MBTA Blue Line subway (followed by a free shuttle) or the Silver Line Bus. to get interesting fares to and from the airport, you can get a CharlieCard. By public transportation, the itinerary between Downton Boston and Logan International Airport (BOS) is about 20 minutes. By car, depending on the traffic it can be 10 minutes. Be sure to plan enough time to reach the airport. By downloading the eDreams App, travel stress-free to the boarding gate, thanks to all the information provided (Terminal, drop-off desk, boarding gate).

Going from O'hare International Airport (ORD) to Downtown Chicago

O'hare International Airport (ORD) is 18 miles away from Downtown Chicago. Should you take a cab or rent a car, it’ll take on average between 30 minutes and 1 hour to reach the city center depending on traffic. The cheapest option is the CTA (Chicago Transport Authority). The Blue Line Train is a 24h service that will lead you close to the city center for $5.

What to do in Chicago

Chicago, also called the Windy City, is the capital city of Illinois. It is located by Lake Michigan. There are thousands of activities to do in Chicago, but if it’s your first time there, you can miss out on the following ones!

Landmarks in Chicago

One of the most famous landmarks in Chicago is “The Bean”, officially known as the Cloud Gate. It is a gigantic archway in Millenium Park. Its reflecting surface is great for selfies! Locals and tourists appreciate going to Millenium Park for a picnic or to watch a concert.

Chicago Riverwalk not only is a nice walk… It’s a lifestyle. Along the 3.4 miles of the Riverwalk, you’ll find plenty of bars, restaurants and even museums. You can also choose to kayak on the river. In the evening, enjoy the sunset while listening to live music.

Best activities to do in Chicago

To go shopping, Chicago has one of the greatest avenues in the world: the Magnificent Mile. In Downtown Chicago, one mile of Michigan Avenue gathers hundreds of stores. From popular brands to small boutiques, from luxury brands to sports stores, everyone can find what they are looking for.

You can’t go to Chicago without trying the famous Chicago-style pizza, and the deep-dish pizza! They both are much thicker than the Italian pizza, which allows lots of place for cheese and other toppings. The difference between the two is the order in which they place the ingredients. Ready to embark for a pizza tasting tour?

Sports fans will be spoilt for choice. Rather basketball or soccer? A baseball fan, which team would you like to watch a White Sox or Chicago Cubs game?

Book now your flight ticket to Chicago at the best price.

How to find cheap flights from Boston (BOS) to Chicago (ORD)

You have to take a last-minute flight for Chicago for business reasons? Or are you just looking for the cheap prices for your trip from Boston to Chicago? eDreams US will help you find the perfect deals for your flight. In just a few clicks compare the flight prices at different dates and with different airlines. If you are booking your trip last-minute, check out the best deals on this page. If you are flexible with your flight dates, be sure to compare the prices between weekdays and the weekend, during the week flights are often cheaper. The price will also often be more advantageous when booking in advance.

Searching for cheap flights on edreams.net is pretty easy. On the search box, enter your departure airport and your destination, choose between a one-way ticket or a return flight, enter the dates of the trip and select the number of passengers. Within a few seconds eDreams’ search engine will display the best deals both regarding the price and the flight duration. You can then personalize the results by adding filters like: the departure time, the airline, or to see only direct flights. Once you find your perfect match, you can go on with your booking. To save money and time, you can directly book a hotel and rent a car.

Frequently asked questions about flights from Chicago to Boston

What are the benefits of booking flexible flight tickets?

Using the flexible flight ticket, you're guaranteed a refund or a rebooking option (without fees) in case of flight cancellations when travelling to United States. At eDreams have you covered!

For flights from Chicago to Boston, how can I find the cheapest price?

The cheapest price for a flight from Chicago to Boston is $37. At eDreams we use different machine learned based methodologies to find our costumers the best option available, considering airline combinations, stopovers and direct flights as well as different criteria for inbound and outbound journeys.

When booking, when is the best time to get the best prices for flights from Chicago to Boston?

The most popular months to book a trip from Chicago to Boston are September, October and May, based on the searches of our customers.

When is the best time to travel from Chicago to Boston?

The best time of the year to visit Boston depends on lots of personal preferences, especially the price. Regarding popularity, October is the best month to fly to Boston from Chicago in terms of searches from our customers, followed by September and July. If you prefer to avoid the busy season and get away from the crowds February, January and April are the months with fewer searches for Chicago - Boston.

How long does the flight from Chicago to Boston take?

Flight length from Chicago to Boston is around 02:27 hours on average, at an average distance of 1,394 km, for flights for the route (which may have 1 or more stops in other cities in between).

Which airports have flights between Chicago and Boston?

The main route from Chicago to Boston is: O hare International Airport (ORD) to Logan International Airport (BOS). The following airlines fly this route: Spirit Airlines. American Airlines. Frontier Airlines. Alternatively, you can find Chicago - Boston flights between Midway Airport (MDW) to Logan International Airport (BOS) with the following airline(s) flying the route: Frontier Airlines.

Which airlines fly from Chicago to Boston?

The airlines that fly non-stop from Chicago to Boston are:

United Airlines.
American Airlines.
Spirit Airlines.

Flying Time 2 h and 27 m When flying from Chicago to Boston, this can take around 2 h and 27 m in flying time, however this flight duration can vary due to other factors

Cheapest flight $37 The best price for flights from Chicago to Boston offered by eDreams, which have been found by our customers in the last 3 days

Departure Airport O'hare International Airport O'hare International Airport is where you'll take off when flying from Chicago to Boston

Arrival Airport Logan International Airport You'll land at Logan International Airport when flying from Chicago to Boston