$100 Cheap flight deals from Chicago (CHI) to Lexington (BOS)
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This Weekend's Flight Deals from Chicago to Lexington
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 $100 One Way, $186 Round Trip from Chicago to Lexington
Prices starting at $186 for return flights and $100 for one-way flights to Lexington were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Lexington economy flight packages
The Cove at Yarmouth by Westgate Resorts
Sep 29 - Oct 2
Chicago (ORD) to Boston (BOS)
Reviewed on Jun 8, 2026
Good Hotels Boston
Sep 24 - Sep 27
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Reviewed on May 23, 2026
The Langham, Boston
Oct 1 - Oct 4
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 6, 2026
Lexington packages with premium economy flights
The Charles Hotel
Sep 24 - Sep 27
Chicago (ORD) to Boston (BOS)
Boston (BOS) to Chicago (ORD)
Battery Wharf Hotel, Boston Waterfront
Sep 24 - Sep 27
Chicago (ORD) to Boston (BOS)
Boston (BOS) to Chicago (ORD)
Reviewed on Aug 7, 2026
Lexington first class flight packages
Sesuit Harbor House
Sep 10 - Sep 18
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 1, 2026
The Mansion at Ocean Edge
Sep 10 - Sep 18
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 7, 2026
More About Flying To Lexington from Chicago
Route Information for Flights from Chicago to Lexington
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | BOS |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Lexington
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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.