$38 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.

Sat, Apr 27 - Sat, May 4
BOS
Logan Intl.
MDW
Midway Intl.
$96 Roundtrip, found 2 days ago
$96
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Apr 27 from Logan Intl. to Midway Intl., returning Sat, May 4, priced at $96 found 2 days ago
Sat, Apr 27 - Sun, Apr 28
BOS
Logan Intl.
ORD
O'Hare Intl.
$201 Roundtrip, just found
$201
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Apr 27 from Logan Intl. to O'Hare Intl., returning Sun, Apr 28, priced at $201 just found
Fri, Apr 26 - Tue, May 7
ORH
Worcester Regional
ORD
O'Hare Intl.
$218 Roundtrip, found 15 hours ago
$218
Roundtrip
found 15 hours ago
Select Delta flight, departing Fri, Apr 26 from Worcester Regional to O'Hare Intl., returning Tue, May 7, priced at $218 found 15 hours ago
Fri, Apr 26 - Sun, Apr 28
MHT
Manchester-Boston Regional
ORD
O'Hare Intl.
$221 Roundtrip, found 1 day ago
$221
Roundtrip
found 1 day ago
Select United flight, departing Fri, Apr 26 from Manchester-Boston Regional to O'Hare Intl., returning Sun, Apr 28, priced at $221 found 1 day ago

Airfares from $38 One Way, $75 Round Trip from Boston to Oak Brook

Prices starting at $75 for return flights and $38 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.

Thu, Jun 6 - Wed, Jun 12
BOS
Boston
ORD
Chicago
$75 Roundtrip, just found
$75
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Jun 6 from Boston to Chicago, returning Wed, Jun 12, priced at $75 just found
Sat, May 4 - Sat, May 11
BOS
Boston
MDW
Chicago
$96 Roundtrip, found 21 hours ago
$96
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Sat, May 4 from Boston to Chicago, returning Sat, May 11, priced at $96 found 21 hours ago
Wed, Aug 21 - Tue, Aug 27
BOS
Boston
ORD
Chicago
$127 Roundtrip, found 1 hour ago
$127
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Aug 21 from Boston to Chicago, returning Tue, Aug 27, priced at $127 found 1 hour ago
Tue, May 14 - Wed, May 15
ORH
Worcester
ORD
Chicago
$191 Roundtrip, found 3 days ago
$191
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, May 14 from Worcester to Chicago, returning Wed, May 15, priced at $191 found 3 days ago
Fri, Apr 26 - Sun, Apr 28
MHT
Manchester
ORD
Chicago
$221 Roundtrip, found 1 day ago
$221
Roundtrip
found 1 day ago
Select United flight, departing Fri, Apr 26 from Manchester to Chicago, returning Sun, Apr 28, priced at $221 found 1 day ago

Oak Brook economy flight packages

DoubleTree by Hilton Chicago - Magnificent Mile
4.0-star property

DoubleTree by Hilton Chicago - Magnificent Mile

8.6/10 Excellent! (2,153 reviews)

Jun 12 - Jun 15

3 night stay

Boston (BOS) to Chicago (ORD)

Spirit Airlines • Coach

Chicago (ORD) to Boston (BOS)

Delta • Coach
Save 100% on your flight
per person
The garage was dark and dengue. The room description said city view. All you could see is a block wall. Orbitz description said the hotel had room service. They don’t. Web Site said no charge for early check in. They charged us $25 The room walls must be thin. We heard people talking from other rooms and in the hall. Anytime a neighbor used the restroom we could hear the water. Basically we got no sleep.

Reviewed on Apr 7, 2024

Congress Plaza Hotel
3.5-star property

Congress Plaza Hotel

7.6/10 Good! (6,529 reviews)

Jun 12 - Jun 15

3 night stay

Boston (BOS) to Chicago (ORD)

Spirit Airlines • Coach

Chicago (ORD) to Boston (BOS)

Delta • Coach
Save 100% on your flight
per person
Very nice rooms and great service

Reviewed on Mar 28, 2024

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

8.8/10 Excellent! (206 reviews)

May 23 - May 27

4 night stay

Boston (BOS) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
per person
Front desk and maintenance staff was amazing super succeeded our expectations i will return gor future dates

Reviewed on Feb 16, 2024

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Prices and availability subject to change. Additional terms may apply.

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
863 mi
Direct Flight Airlines
American Airlines, KLM, Qatar Airways, JAL, Emirates, Delta Air Lines, Air New Zealand, United Airlines, Alaska Airlines, Etihad Airways, JetBlue, Cathay Pacific, SAS, Royal Jordanian, Iberia, Hawaiian Airlines, ANA, Korean Air, TAP Air Portugal, Virgin Atlantic, British Airways
Earliest Flight Arrival
11:54AM UTC
Latest Flight Arrival
2:52AM UTC

Boston to Oak Brook

Great Deals on Flights From Boston to Oak Brook

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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.