
$145 Cheap flight deals from Chicago (CHI) to York (BOS)
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This Weekend's Flight Deals from Chicago to York
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 $145 One Way, $337 Round Trip from Chicago to York
Prices starting at $337 for return flights and $145 for one-way flights to York were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
York economy flight packages


Hilton Garden Inn Freeport Downtown
Dec 17 - Dec 20
Chicago (ORD) to Portland (PWM)
Reviewed on Nov 5, 2026

More About Flying To York from Chicago
Route Information for Flights from Chicago to York
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | BOS |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to York
If you are looking online for bargain Chicago to York flights, Orbitz is your ideal destination. We understand that vacations can be expensive and offer guaranteed low prices on our domestic and international tickets.
Orbitz Uses Cutting-Edge Mobile Tools
Orbitz may offer low cost Chicago to York flights but this does not mean that we skimp on giving you the latest mobile apps. You don’t have to worry about checking your flight status as we send the info for your flights from Chicago to York directly to your smartphone.
Fly Cheap and Earn Miles on Your Chicago to York Flights
Frequent flyer miles and points are great—and even better when you earn them on cheap flights from Chicago to York. With Orbitz, you can earn miles for your frequent flyer program on qualified flights. Enter your frequent flyer number when you book with us to get rewarded for your flight.
Orbitz Takes the Hassle Out Of Flying
We know that flying can be stressful, particularly if you are traveling with young children. That’s why we make sure you are aware of any changes or delays to your flights from Chicago to York via your phone or email address. We can even inform family members too.
Orbitz Flights Fit Around Your Lifestyle
Orbitz understands that you don’t necessarily want to fly at 5:00 a.m—and that sometimes you do. This is why we allow you to find the best Chicago to York flights at the times you want with ease.
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Los Angeles
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- Chicago to New Orleans
- Chicago to Washington
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- Chicago to Paris
- Chicago to Rome
- Chicago to Toronto
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- Chicago to Sacramento
- Chicago to Montreal
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- Chicago to Atlantic City
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York Airports
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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.

