$154 Cheap flight deals from Chicago (CHI) to York (BOS)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
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 $154 One Way, $297 Round Trip from Chicago to York
Prices starting at $297 for return flights and $154 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
Saco Bay Hotel
Jun 23 - Jun 27
Chicago (CHI) to Portland (PWM)
Reviewed on May 9, 2026
Ogunquit River Inn & Suites
Jun 23 - Jun 27
Chicago (CHI) to Portland (PWM)
Reviewed on Sep 14, 2025
Portland Harbor Hotel
Jun 23 - Jun 27
Chicago (CHI) to Portland (PWM)
Reviewed on Dec 8, 2025
York first class flight packages
The Docent's Collection at 121 Middle Street
Jun 26 - Jun 30
Chicago (CHI) to Portland (PWM)
Portland (PWM) to Chicago (CHI)
Reviewed on Mar 31, 2026
Portland Harbor Hotel
Jun 26 - Jun 30
Chicago (CHI) to Portland (PWM)
Portland (PWM) to Chicago (CHI)
Reviewed on Dec 8, 2025
Canopy by Hilton Portland Waterfront
Jun 26 - Jun 30
Chicago (CHI) to Portland (PWM)
Portland (PWM) to Chicago (CHI)
Reviewed on Aug 25, 2025
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
Whether you want to book cheap flights from Chicago to York or are looking for the perfect package holiday, Orbitz is your one-stop source. Taking the stress and expense out of travel, Orbitz helps you find the best fares for Chicago to York flights.
Make the Most of Your Vacation
Not only does Orbitz have cheap deals for Chicago to York flights, we can also help you plan your vacation in advance. Why wait in lengthy lines for tickets to shows, amusement parks, and other attractions when you could be making the most of your holiday? Add activities to your flight booking for fewer hassles once you arrive in York.
Planning on the Go
Book your flights from Chicago to York wherever you are with the Orbitz app for Android and iPhone. Or simply use m.orbitz.com on your mobile browser to search and book the Chicago to York flights that you want. And if you’re running late, you check your flight status and baggage claim information on your mobile device too too.
Craft Your Perfect Vacation
Orbitz takes the stress out of vacation planning with great deals on flights from Chicago to York, hotels, car rentals, cruises, and more. Mix and match results for your perfect trip, or book a complete vacation package.
Keep Informed With Orbitz
With Orbitz’s free alerts service, you will stay informed of flight or services disruptions to your Chicago to York flights. The alerts can be sent straight to your mobile phone or email.
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to New Orleans
- Chicago to London
- Chicago to Washington
- Chicago to Paris
- Chicago to Toronto
- Chicago to Rome
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Sacramento
- Chicago to Kansas City
- Chicago to Hartford
- Chicago to Atlantic City
York Airports
More Destinations
- Flights from Nashville to York Beach
- Flights from Phoenix to York Beach
- Flights from Raleigh to York Beach
- Flights from Pittsburgh to York Beach
- Flights from Fort Lauderdale to York Beach
- Flights from Evansville to Ogunquit
- Flights from Boston to Ogunquit
- Flights from Chicago to Ogunquit
- Flights from Cleveland to Ogunquit
- Flights from Columbus to Ogunquit
- Flights from Detroit to Ogunquit
- Flights from Houston to Ogunquit
- Flights from Indianapolis to Ogunquit
- Flights from London to Ogunquit
- Flights from Los Angeles to Ogunquit
- Flights from Minneapolis - St. Paul to Ogunquit
- Flights from New York to Ogunquit
- Flights from Philadelphia to Ogunquit
- Flights from Phoenix to Ogunquit
- Flights from Portland to Ogunquit
- Flights from Pittsburgh to Ogunquit
- Flights from Fort Lauderdale to Ogunquit
- Flights from Tulsa to Ogunquit
- Flights from Panama City to Ogunquit
- Flights from Allentown to Ogunquit
- Flights from Tampa to Ogunquit
- Flights from Jacksonville to Ogunquit
- Flights from Lexington to Ogunquit
- Flights from San José to Ogunquit
- Flights from Greenville - Spartanburg to Ogunquit
- Flights from Newport News to Ogunquit
- Flights from Chattanooga to Ogunquit
- Flights from Charlotte to Kittery
- Flights from Chicago to Kittery
- Flights from Minneapolis - St. Paul to Kittery
- Flights from New Orleans to Kittery
- Flights from New York to Kittery
- Flights from Philadelphia to Kittery
- Flights from Phoenix to Kittery
- Flights from Toronto to Kittery
- Flights from Newark to Kittery
- Flights from Newport News to Kittery
- Flights from Alexandria to Kennebunkport
- Flights from Austin to Kennebunkport
- Flights from Las Vegas to Kennebunkport
- Flights from Miami to Kennebunkport
- Flights from Nashville to Kennebunkport
- Flights from Philadelphia to Kennebunkport
- Flights from Salt Lake City to Kennebunkport
- Flights from San Antonio to Kennebunkport
- Flights from Jackson to Kennebunkport
- Flights from Montego Bay to Kennebunkport
- Flights from Palm Springs to Kennebunkport
- Flights from St. George to Kennebunkport
- Flights from Richmond to Kennebunkport
- Flights from Santa Barbara to Kennebunkport
- Flights from Daytona Beach to Kennebunkport
- Flights from Milwaukee to Kennebunkport
- Flights from Reno to Kennebunkport
- Flights from Springfield to Kennebunkport
- Flights from Oklahoma City to Kennebunkport
- Flights from Allentown to Kennebunkport
- Flights from Birmingham to Kennebunkport
- Flights from Tucson to Kennebunkport
- Flights from Grand Rapids to Kennebunkport
- Flights from Savannah to Kennebunkport
- Flights from Asheville to Kennebunkport
- Flights from Salisbury to Kennebunkport
- Flights from Bozeman to Kennebunkport
- Flights from Green Bay to Wells
- Flights from Charlotte to Wells
- Flights from Chicago to Wells
- Flights from Washington to Wells
- Flights from Columbus to Wells
- Flights from Baltimore to Cape Neddick
- Flights from Chicago to Cape Neddick
- Flights from Houston to Cape Neddick
- Flights from Los Angeles to Cape Neddick
- Flights from Minneapolis - St. Paul to Cape Neddick
- Flights from New York to Cape Neddick
- Flights from Philadelphia to Cape Neddick
- Flights from Portland to Cape Neddick
- Flights from Raleigh to Cape Neddick
- Flights from Toronto to Cape Neddick
- Flights from Washington to Cape Neddick
- Flights from Newark to Cape Neddick
- Flights from Grand Rapids to Cape Neddick
- Flights from Chicago to Sanford
- Flights from Cincinnati to Sanford
- Flights from Dallas to Sanford
- Flights from Detroit to Sanford
- Flights from Miami to Sanford
- Flights from Nashville to Sanford
- Flights from New York to Sanford
- Flights from Portland to Sanford
- Flights from Raleigh to Sanford
- Flights from Fort Lauderdale to Sanford
- Flights from South Bend to Sanford
- Flights from Tampa to Sanford
- Flights from Lansing to Sanford
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.