
$59 Cheap flight deals from Boston (BOS) to Chicago (CHI)
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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 $59 One Way, $83 Round Trip from Boston to Chicago
Prices starting at $83 for return flights and $59 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.
Chicago economy flight packages

Swissotel - Chicago
Dec 15 - Dec 19
Boston (BOS) to Chicago (ORD)
Reviewed on Sep 3, 2025

Hotel Riu Plaza Chicago
Dec 15 - Dec 19
Boston (BOS) to Chicago (ORD)
Reviewed on Sep 2, 2025

Hilton Chicago O'Hare Airport
Dec 5 - Dec 7
Boston (BOS) to Chicago (ORD)
Reviewed on Sep 14, 2025
More About Flying To Chicago from Boston
Route Information for Flights from Boston to Chicago
Origin Airport IATA Code | BOS |
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Destination Airport IATA Code | CHI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Flights from Boston to Chicago
Staying on budget when planning a trip can be a challenge, but Orbitz.com 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 Orbitz.com. 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 Orbitz.com.
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 Orbitz.com 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
Flights to Chicago
- New York to Chicago
- Dallas to Chicago
- Houston to Chicago
- Phoenix to Chicago
- Toronto to Chicago
- Orlando to Chicago
- Las Vegas to Chicago
- San Francisco to Chicago
- Los Angeles to Chicago
- Washington to Chicago
- Detroit to Chicago
- New Orleans to Chicago
- Montreal to Chicago
- Kansas City to Chicago
- Sacramento to Chicago
- Hartford to Chicago
- London to Chicago
- Paris to Chicago
- Harrisburg - Hershey to Chicago
- Rome to Chicago
Flights from Boston
- Boston to Orlando
- Boston to London
- Boston to Los Angeles
- Boston to Miami
- Boston to Chicago
- Boston to New York
- Boston to Atlanta
- Boston to Paris
- Boston to Toronto
- Boston to Dallas
- Boston to Rome
- Boston to Houston
- Boston to Detroit
- Boston to Montreal
- Boston to Madrid
- Boston to Beijing
- Boston to Sao Paulo
- Boston to Kansas City
- Boston to Buenos Aires
- Boston to Berlin
More Destinations
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- Flights from Boston (BOS) to Chicago (ORD)
- Flights from Charleston (CHS) to Chicago (ORD)
- Flights from Cedar Rapids (CID) to Chicago (ORD)
- Flights from Charlotte (CLT) to Chicago (ORD)
- Flights from Columbus (CMH) to Chicago (ORD)
- Flights from Columbia (COU) to Chicago (ORD)
- Flights from Cincinnati (CVG) to Chicago (ORD)
- Flights from Dallas (DAL) to Chicago (ORD)
- Flights from Delhi (DEL) to Chicago (ORD)
- Flights from Denver (DEN) to Chicago (ORD)
- Flights from Des Moines (DSM) to Chicago (ORD)
- Flights from Detroit (DTW) to Chicago (ORD)
- Flights from Dubai (DXB) to Chicago (ORD)
- Flights from Grand Rapids (GRR) to Chicago (ORD)
- Flights from White Plains (HPN) to Chicago (ORD)
- Flights from Seoul (ICN) to Chicago (ORD)
- Flights from Jacksonville (JAX) to Chicago (ORD)
- Flights from Chennai (MAA) to Chicago (ORD)
- Flights from Kansas City (MCI) to Chicago (ORD)
- Flights from Harrisburg (MDT) to Chicago (ORD)
- Flights from Miami (MIA) to Chicago (ORD)
- Flights from Milwaukee (MKE) to Chicago (ORD)
- Flights from Madison (MSN) to Chicago (ORD)
- Flights from Ontario (ONT) to Chicago (ORD)
- Flights from West Palm Beach (PBI) to Chicago (ORD)
- Flights from Portland (PDX) to Chicago (ORD)
- Flights from Beijing (PEK) to Chicago (ORD)
- Flights from Peoria (PIA) to Chicago (ORD)
- Flights from Shanghai (PVG) to Chicago (ORD)
- Flights from San Diego (SAN) to Chicago (ORD)
- Flights from San Antonio (SAT) to Chicago (ORD)
- Flights from Savannah (SAV) to Chicago (ORD)
- Flights from Louisville (SDF) to Chicago (ORD)
- Flights from San Jose (SJC) to Chicago (ORD)
- Flights from Salt Lake City (SLC) to Chicago (ORD)
- Flights from Sacramento (SMF) to Chicago (ORD)
- Flights from St. Louis (STL) to Chicago (ORD)
- Flights from Trenton (TTN) to Chicago (ORD)
- Flights from Knoxville (TYS) to Chicago (ORD)
- Flights from Vancouver (YVR) to Chicago (ORD)
- Flights from Buffalo (BUF) to Chicago (MDW)
- Flights from Charlotte (CLT) to Chicago (MDW)
- Flights from Cincinnati (CVG) to Chicago (MDW)
- Flights from Houston (HOU) to Chicago (MDW)
- Flights from Indianapolis (IND) to Chicago (MDW)
- Flights from Jackson (JAN) to Chicago (MDW)
- Flights from Marion (MWA) to Chicago (MDW)
- Flights from Oklahoma City (OKC) to Chicago (MDW)
- Flights from Sarasota (SRQ) to Chicago (MDW)
- Flights from Tampa (TPA) to Chicago (MDW)
- Flights from Guadalajara to Oak Park
- Flights from Atlanta to Oak Park
- Flights from Boston to Oak Park
- Flights from Dallas to Oak Park
- Flights from Helsinki to Oak Park
- Flights from Miami to Oak Park
- Flights from Philadelphia to Oak Park
- Flights from Phoenix to Oak Park
- Flights from San Francisco to Oak Park
- Flights from Seattle to Oak Park
- Flights from Fort Lauderdale to Oak Park
- Flights from Oakland to Oak Park
- Flights from Savannah to Oak Park
- Flights from Shenzhen to Oak Park
- Flights from Beijing to Evanston
- Flights from Miami to Evanston
- Flights from Orlando to Evanston
- Flights from Portland to Evanston
- Flights from Raleigh to Evanston
- Flights from Fort Lauderdale to Evanston
- Flights from Savannah to Evanston
- Flights from Atlanta to Cicero
- Flights from Austin to Cicero
- Flights from Baltimore to Cicero
- Flights from Beijing to Cicero
- Flights from Boston to Cicero
- Flights from Charlotte to Cicero
- Flights from Dallas to Cicero
- Flights from Denver to Cicero
- Flights from Houston to Cicero
- Flights from Las Vegas to Cicero
- Flights from Los Angeles to Cicero
- Flights from New York to Cicero
- Flights from Philadelphia to Cicero
- Flights from Phoenix to Cicero
- Flights from San Francisco to Cicero
- Flights from Boston to Glenview
- Flights from Houston to Glenview
- Flights from Miami to Glenview
- Flights from Tampa to Glenview
- Flights from Atlanta to Southwest Side
- Flights from Dallas to Southwest Side
- Flights from Phoenix to Southwest Side
- Flights from San Francisco to Southwest Side
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.



