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Boston to Chicago Flights

Find cheap tickets for flights from Boston to Chicago at CheapTickets. Why shop around when the low fares are handed to you?

Logan International Airport (BOS) is presently the only airport with bargain commercial Boston to Chicago flights via American Airlines. A 12-year top-to-bottom update project by Massachusetts Port Authority (Massport) was concluded only six years ago. Passengers departing on domestic flights from Boston to Chicago will most likely notice the parking garage, terminals, and arrival and departure roadway improvements. American Airlines operates an Admirals Club in Terminal B North for passengers waiting to board budget Boston to Chicago flights, which usually depart from Gates B22-36. Logan strives to improve the customer experience, and has been noted for the variety of choices available for arrival and departure transport, and its on-time departure record.

O'Hare International Airport (ORD) and Midway International Airport (MDW) both receive incoming low cost flights from Boston to Chicago. Discount carriers JetBlue Airways and Spirit Airlines share gate 3L with American Airlines, which also utilizes Gates 3H and 3K. United Airlines and their affiliate United Express and subcontractor Shuttle America keep to Gates 1B and 1C. Southwest Airlines Boston to Chicago flights arrive at Midway's A and B concourses. Travelers exiting Midway enjoy convenient access to the central business district and Loop through Stevenson Expressway and Chicago Transit Authority's (CTA) Orange Line elevated trains. CTA also uses the Midway station for bus service to several stops in the vicinity.

Cheap flights from Boston to Chicago

Prices are for round-trip flights per adult (taxes and fees included)

Cheapest fares highlighted below

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Next July
Sun Mon Tue Wed Thu Fri Sat
26 27 28 29 30 31 1 $168
2 $168 3 $148 4 $148 5 $148 6 $148 7 $168 8 $168
9 $208 10 $168 11 $148 12 $158 13 $188 14 $173 15 $173
16 $183 17 $153 18 $148 19 $148 20 $190 21 $212 22 $190
23 $222 24 $190 25 $188 26 $188 27 $193 28 $232 29 $198
30 1 2 3 4 5 6

Fare, taxes & fees: Fares were found on CheapTickets.com and are updated nightly. They include all taxes and fees, except baggage fees.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by CheapTickets. 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.

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