$286 Economy Roundtrip to Chicago (BOS-CHIA) in Oct from Boston

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$286 Economy Roundtrip to Chicago (BOS-CHIA) in Oct from Boston

Best Flights starting from $286

from$286economy

Boston (BOS)

Sat, Oct 10

Roundtrip

Chicago (Any)

Sun, Oct 11

Fields updated — click View Prices to search ↑

Other Options for This Route

CHIA destination

Economy One-way to Chicago (Any)

Boston (BOS) to Chicago (Any) in October from $95

CHIA destination

Economy Roundtrip to Chicago (Any)

Boston (BOS) to Chicago (Any) in December from $71

CHIA destination

Economy Roundtrip to Chicago (Any)

Boston (BOS) to Chicago (Any) in March from $81

CHIA destination

Economy Roundtrip to Chicago (Any)

Boston (BOS) to Chicago (Any) in April from $157

CHIA destination

Economy Roundtrip to Chicago (Any)

Boston (BOS) to Chicago (Any) in May from $81

CHIA destination

Economy Roundtrip to Chicago (Any)

Boston (BOS) to Chicago (Any) in September from $196

Other Destinations

FLL destination

Economy One-way to Fort Lauderdale (FLL)

Boston (BOS) to Fort Lauderdale (FLL) in October from $44

DCA destination

Economy One-way to Washington, D.C. (DCA)

Boston (BOS) to Washington, D.C. (DCA) in October from $59

FLL destination

Economy Roundtrip to Fort Lauderdale (FLL)

Boston (BOS) to Fort Lauderdale (FLL) in October from $68

PHL destination

Economy Roundtrip to Philadelphia (PHL)

Boston (BOS) to Philadelphia (PHL) in October from $71

MCO destination

Economy Roundtrip to Orlando (MCO)

Boston (BOS) to Orlando (MCO) in October from $73

BWI destination

Economy Roundtrip to Washington, D.C. (BWI)

Boston (BOS) to Washington, D.C. (BWI) in October from $77

Flights from Other Cities

CHIA destination

Economy One-way to Chicago (Any)

Fort Lauderdale (Any) to Chicago (Any) in October from $56

CHIA destination

Economy One-way to Chicago (Any)

Miami (Any) to Chicago (Any) in October from $56

CHIA destination

Economy One-way to Chicago (Any)

New York (JFK) to Chicago (Any) in October from $63

CHIA destination

Economy One-way to Chicago (Any)

Fort Lauderdale (FLL) to Chicago (Any) in October from $64

CHIA destination

Economy One-way to Chicago (Any)

Orlando (Any) to Chicago (Any) in October from $74

CHIA destination

Economy One-way to Chicago (Any)

New York (Any) to Chicago (Any) in October from $88

Cheap economy Class Flights from Boston (BOS) to Chicago (Any) October

Find the best deals on economy class flights. Compare prices for direct flights, one-stop, and multi-stop options.

Cheap economy Flights: BOS to CHIA in October - Route 1

Starting from $286

Flight Options & Prices:

Direct Flights: From $326 - Fastest option with no layovers
One-Stop Flights: From $286 - Good value with one connection
Multi-Stop Flights: From $286 - Cheapest option with multiple connections

Book your economy class flight from Boston (BOS) to Chicago (Any)and save money on your travel. Compare all flight options to find the best deal for your october trip.

Why Choose Economy Class Flights from Boston (BOS) to Chicago (Any)?

Compare prices from multiple airlines
Find direct flights and multi-stop options
Best deals for october travel
Flexible booking options
24/7 customer support

Planning a trip from Boston (BOS) to Chicago (Any) in october? SlickTrip helps you find the cheapest economy class flights with our comprehensive flight comparison tool. Whether you prefer direct flights for convenience or multi-stop flights for savings, we have options for every budget and schedule.