Cheap Flight Deals From Boston (BOS) to Chicago (CHI) Starting at $44

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This Weekend's Flight Deals from Boston to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $44 One Way, $82 Round Trip from Boston to Chicago

Prices starting at $82 for return flights and $44 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

More About Flying To Chicago from Boston

Route Information for Flights from Boston to Chicago

Origin Airport IATA Code
Destination Airport IATA Code
863 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Icelandair, Emirates, Delta Air Lines, Air New Zealand, United Airlines, Alaska Airlines, JetBlue Airways, LATAM Airlines, SAS, Royal Jordanian, Iberia, Hawaiian Airlines, ANA, Korean Air, TAP Air Portugal, WestJet, Virgin Atlantic, British Airways
Earliest Flight Arrival
11:29AM UTC
Latest Flight Arrival
2:44AM UTC

Flights from Boston to Chicago

Staying on budget when planning a trip can be a challenge, but makes it a little easier. You will discover cheap flights from Boston to Chicago as well as discount ground transportation and accommodations. Chicago is home to more than 2.7 million people, making it the third-largest city in the United States.

Boston Information

When you leave Boston, you will depart from the Logan International Airport, which is located on the east side of Boston. It is host to several airlines, including Delta, Spirit, American, JetBlue, US Airways, and AirTran. All these airlines provide air service to Chicago, and their best rates can be found on The most convenient public transportation option for getting to the airport is the T Bus, which costs $2 from downtown. Numerous taxi companies are readily available, and their rates range from $25 to $35 from downtown.

Abundant parking spaces are available at the airport, including short-term, long-term, and economy parking. Economy has the cheapest rate of $18 per day, and regular parking will cost about $27 daily. Whether you want a quick snack or a full meal, you will discover a variety of restaurants and menu items inside the terminals. Johnny Rockets, Ozone, Boston Beer Works, and Asian Too are a few of your options, and you'll find pizzas, burgers, and more.

Chicago Information

Chicago is a fun and exciting city to visit and has so much to enjoy. Whether you enjoy sports, classical music, or modern architecture, Chicago is the place to be. Located in northern Illinois, Chicago borders Lake Michigan, which provides a variety of water activities. The city has a rich history and diverse culture visitors will enjoy.

When you plan your flight to Chicago, you have two airports to choose from: Chicago O'Hare International Airport and Chicago Midway International Airport. O'Hare is located about 17 miles northwest of downtown, and Midway is 8 miles from downtown. Ground transportation from both airports is offered by way of train, taxi, and shuttle. The CTA trains provide fast and convenient transportation from the airport for $2.25 or less. Taxi fares average about $40 to downtown from O'Hare and $25 from Midway. Shuttle service is provided by Go Airport Express and Omega Airport Shuttle, and their average rate is $25 from O'Hare and $15 from Midway. Most major car rental companies are located at both airports, and you can arrange for a car in advance when you book your flight with

The weather in Chicago ranges from cold in the winter to warm in summer. The coldest month is January, during which the average temperature ranges from nightly lows in the teens to daytime highs of around 31 degrees Fahrenheit. July is the warmest month and has average temperatures in the mid-80s. The months of May through August each receive around 4 inches of rainfall. January and February only receive about 2 inches of precipitation, but it is usually in the form of snow.

Chicago has an extensive list of attractions everyone will enjoy. Theater enthusiasts will enjoy the Chicago Shakespeare Theater located on Navy Pier and the Lookingglass Theatre Company. If you enjoy water sports, check out the many attractions on Lake Michigan. Kid and adults will have a great time watching a ballgame at Wrigley Field or spending a day at the Lincoln Zoo.

Start Planning Your Trip to Chicago

Let help save you time and money when you are planning your trip from Boston to Chicago. You will discover discounts on flights, ground transportation, and hotel accommodations. Take a break from your everyday life, and start planning a fun trip to the Windy City.

Frequently asked questions

Am I able to catch a flight from Boston to Chicago now?
If you’re agonizing over quarantine requirements and travel restrictions when getting a flight from Boston to Chicago, check out the Covid-19 Travel Advisor.
Are there non-stop flights from Boston to Chicago?
Direct flights are available with 4 airlines from Boston, MA (BOS-Logan Intl.) to O’Hare Intl. Airport (ORD), which means you could be booking the vacation of your dreams within minutes. Here are some popular carriers to check out:

  • United Airlines
  • American Airlines
  • Delta
  • JetBlue

What is the shortest flight from Boston to Chicago?
The quickest flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.) is around 3 hours and 19 minutes. Grab a refreshment from the cabin crew, hone your travel itinerary or read a few magazines — you’ll have enough time on this medium-haul trip.
What airlines fly from Boston to Chicago most frequently?
Here are the airlines that fly the most frequently between Boston and Chicago. Find out which one best meets your needs: United Airlines - (UA) with 208 flights every month American Airlines - (AA) with 195 flights every month Delta - (DL) with 147 flights every month JetBlue - (B6) with 56 flights every month
If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Chicago with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.