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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
Rodeway Inn Logan International Airport
2.0 out of 5.0Fri, Jun 15 - Tue, Jun 19
ORD - BOS
$460
per person
Modern 3BR in Downtown Crossing by Sonder
3.5 out of 5.0Fri, Jun 15 - Tue, Jun 19
ORD - BOS
$1,418
per person
Club Quarters Hotel in Boston
4.0 out of 5.0Fri, May 25 - Tue, May 29
ORD - BOS
$702
per person
Courtyard by Marriott Boston-Cambridge
3.5 out of 5.0Wed, May 23 - Sun, May 27
ORD - BOS
$1,091
per person
Surfside Hotel and Suites
2.5 out of 5.0Fri, Jun 1 - Wed, Jun 6
ORD - BOS
$553
per person
The Inn at Longwood Medical
3.5 out of 5.0Fri, Jun 1 - Wed, Jun 6
ORD - BOS
$742
per person
The Dan'l Webster Inn and Spa
3.5 out of 5.0Fri, Jun 1 - Wed, Jun 6
ORD - BOS
$497
per person
Crowne Pointe Historic Inn & Spa
4.0 out of 5.0Fri, Jun 1 - Wed, Jun 6
ORD - BOS
$810
per person
Brass Key Guesthouse - Adults Only
4.0 out of 5.0Fri, Jun 1 - Wed, Jun 6
ORD - BOS
$774
per person
More to explore for Chicago to Boston
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Flights from Cities near Chicago
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Other Flights to Boston
- Chicago to Boston
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- Washington to Boston
- Detroit to Boston
- Fort Lauderdale to Boston
- New York to Boston
- Minneapolis - St. Paul to Boston
- Denver to Boston
- Seattle to Boston
- Houston to Boston
- Dallas to Boston
- Baltimore to Boston
- Philadelphia to Boston
- Orlando to Boston
- Atlanta to Boston
- San Francisco to Boston
* Savings based on all holiday package bookings with Flight + Hotel on Orbitz.com from July 1, 2015 to June 30, 2016, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.
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.
