$51 Cheap flight deals from Chicago (CHI) to Essex (BOS)
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This Weekend's Flight Deals from Chicago to Essex
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 $51 One Way, $110 Round Trip from Chicago to Essex
Prices starting at $110 for return flights and $51 for one-way flights to Essex were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Essex economy flight packages
The Revolution Hotel
Dec 27 - Dec 30
Chicago (CHI) to Boston (BOS)
Reviewed on Oct 30, 2025
The Whitney Hotel
Dec 28 - Dec 30
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Reviewed on Jul 30, 2024
The Bostonian Boston
Dec 27 - Dec 30
Chicago (CHI) to Boston (BOS)
Reviewed on Oct 19, 2025
More About Flying To Essex from Chicago
Route Information for Flights from Chicago to Essex
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | BOS |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Essex
The perfect trip begins with Orbitz. From booking your flights from Chicago to Essex to finding the best hotels, Orbitz has got it covered.
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With an easy to use system, Orbitz takes the stress and expense out of travel. Not only does Orbitz match your Chicago to Essex flights to your ideal hotel, the Display Matrix shows your deals and discounts, including free nights and other savings.
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Not only does booking with us ensure guaranteed low prices, but Orbitz does the hard work, leaving you to relax. Just tell us what you want, from Chicago to Essex flights, to great deals on hotels and car rental, and activities and tours, and we will do all the rest.
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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.