$95 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 $95 One Way, $182 Round Trip from Chicago to Lexington
Prices starting at $182 for return flights and $95 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
Raffles Boston
Nov 12 - Nov 15
Chicago (CHI) to Boston (BOS)
Reviewed on Sep 21, 2026
Four Seasons Hotel Boston
Nov 12 - Nov 15
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Lexington first class flight packages
Boston Harbor Hotel
Oct 23 - Oct 26
Chicago (ORD) to Boston (BOS)
Boston (BOS) to Chicago (ORD)
Reviewed on Sep 22, 2026
The Langham, Boston
Oct 23 - Oct 26
Chicago (ORD) to Boston (BOS)
Boston (BOS) to Chicago (ORD)
Reviewed on Sep 22, 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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You can always find affordable flights from Chicago to Lexington on Orbitz. Use different airlines to book arrival and departure flights, take advantage of vacation package deals, and secure exclusive rewards.
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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.