$68 Cheap flight deals from Boston (BOS) to Oak Brook (CHI)
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This Weekend's Flight Deals from Boston to Oak Brook
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 $68 One Way, $137 Round Trip from Boston to Oak Brook
Prices starting at $137 for return flights and $68 for one-way flights to Oak Brook were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Oak Brook economy flight packages
Hotel Riu Plaza Chicago
May 22 - May 24
Boston (BOS) to Chicago (ORD)
Chicago (ORD) to Boston (BOS)
Reviewed on Jan 14, 2026
LondonHouse Chicago, Curio Collection by Hilton
May 14 - May 18
Boston (BOS) to Chicago (ORD)
Reviewed on Mar 9, 2026
Pendry Chicago
May 21 - May 24
Boston (BOS) to Chicago (ORD)
Chicago (ORD) to Boston (BOS)
Reviewed on Feb 25, 2026
More About Flying To Oak Brook from Boston
Route Information for Flights from Boston to Oak Brook
Origin Airport IATA Code | BOS |
|---|---|
Destination Airport IATA Code | CHI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Boston to Oak Brook
It has never been easier to find cheap Boston to Oak Brook flights. Orbitz has some of the best deals around to save you more money on your flight, hotel, and vacation package for the trip you have been waiting for.
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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.