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Selected fares from Chicago to Boston
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Orbitz is the best online spot to find cheap tickets to put the wind beneath your wings for flights from Chicago to Boston you'll have a few extra bucks in your back pocket when you land in Beantown.
The Windy City offers two options for budget fares for your Chicago to Boston flight, depending on your location and personal tastes. O'Hare International Airport (ORD) is in the northwest corner, 17 miles from the downtown loop. Midway International Airport (MDW) is on the southwest side, eight miles from the loop. Budget-conscious planners who opt for O'Hare will find that the bustling airport, the world's second largest, is a hub for United Airlines and American Airlines and that the smaller Midway is a hub for Southwest Airlines. Your Chicago to Boston flight could be on any of the major airlines, because they all serve Massachusetts' capital city with direct flights. O'Hare offers the best in airport accommodations with a handful of lounges, classic American and international food, and a lot of specialty shops to procure a one-of-a-kind souvenir.
Even though the two-hour nonstop Chicago to Boston flight is a domestic route, you will step into a historic city known as the Athens of America when you land at Logan International Airport (BOS). Aviation.com dubbed Logan the "Easiest Airport to Get To" in 2007 because of its transportation options, including rental cars, cabs, vans, limos and several options from the Massachusetts Bay Transportation Authority (MBTA) like the Blue line train, the Silver line train, and the ferry. That means it is easy to enjoy your flight from Chicago to Boston without having to think about any other hassles, whether you're traveling the three miles to downtown or you're a budget planner who plotted tours of the City on a Hill when you booked tickets. If you're coming from Chicago, the weather in Boston will be nothing new, but chances are you'll want to book your flight from Chicago to Boston in the summer.
Save more with Boston Flight + Hotel packages
Bedford Plaza Hotel - Boston
2.5 out of 5.0Wed, Dec 6 - Thu, Dec 14
CHI-All Airports - Logan Intl.
$373
per person
Hilton Boston/Dedham
3.5 out of 5.0Wed, Nov 29 - Mon, Dec 4
O'Hare Intl. - Logan Intl.
$393
per person
The Ritz-Carlton, Boston
5.0 out of 5.0Wed, Dec 6 - Thu, Dec 14
CHI-All Airports - Logan Intl.
$2,110
per person
Boston Marriott Burlington
3.5 out of 5.0Wed, Dec 6 - Thu, Dec 14
CHI-All Airports - Logan Intl.
$860
per person
Courtyard by Marriott Boston Logan Airport
3.0 out of 5.0Wed, Dec 6 - Thu, Dec 14
CHI-All Airports - Logan Intl.
$617
per person
Royal Sonesta Boston
4.0 out of 5.0Wed, Dec 6 - Thu, Dec 14
CHI-All Airports - Logan Intl.
$924
per person
Red Roof PLUS+ Boston - Woburn
2.5 out of 5.0Wed, Dec 6 - Thu, Dec 14
CHI-All Airports - Logan Intl.
$405
per person
Sheraton Needham Hotel
3.5 out of 5.0Wed, Dec 6 - Thu, Dec 14
CHI-All Airports - Logan Intl.
$770
per person
Taj Boston
4.5 out of 5.0Wed, Dec 6 - Thu, Dec 14
CHI-All Airports - Logan Intl.
$786
per person
Club Quarters Hotel in Boston
4.0 out of 5.0Wed, Dec 6 - Thu, Dec 14
CHI-All Airports - Logan Intl.
$786
per person
The Westin Boston Waterfront
4.0 out of 5.0Thu, Nov 23 - Tue, Nov 28
O'Hare Intl. - Logan Intl.
$649
per person
More to explore for Chicago to Boston
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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.
