$83 Cheap flight deals from Boston (BOS) to Addison (CHI)
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This Weekend's Flight Deals from Boston to Addison
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.
BOS
Logan Intl.
MDW
Midway Intl.
$207 Roundtrip, found 1 day ago
$207
Roundtrip
found 1 day ago
BOS
Logan Intl.
ORD
O'Hare Intl.
$273 Roundtrip, found 5 hours ago
$273
Roundtrip
found 5 hours ago
PVD
T.F. Green
ORD
O'Hare Intl.
$539 Roundtrip, found 6 hours ago
$539
Roundtrip
found 6 hours ago
PVD
T.F. Green
MDW
Midway Intl.
$896 Roundtrip, found 6 hours ago
$896
Roundtrip
found 6 hours ago
Airfares from $83 One Way, $157 Round Trip from Boston to Addison
Prices starting at $157 for return flights and $83 for one-way flights to Addison were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
BOS
Boston
ORD
Chicago
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
BOS
Boston
MDW
Chicago
$163 Roundtrip, found 9 hours ago
$163
Roundtrip
found 9 hours ago
BOS
Boston
ORD
Chicago
$168 Roundtrip, found 6 days ago
$168
Roundtrip
found 6 days ago
BOS
Boston
ORD
Chicago
$180 Roundtrip, found 2 days ago
$180
Roundtrip
found 2 days ago
ORH
Worcester
ORD
Chicago
$204 Roundtrip, found 1 day ago
$204
Roundtrip
found 1 day ago
Addison economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
9.4/10 Exceptional! (2,401 reviews)
Apr 30 - May 3
3 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $790, price is now $581 per person
$581
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.
Reviewed on Nov 3, 2025
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (3,495 reviews)
Apr 30 - May 3
3 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,044, price is now $663 per person
$663
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.
Reviewed on Jan 14, 2026
4.0-star property
Eurostars Magnificent Mile
9/10 Wonderful! (3,314 reviews)
Apr 30 - May 3
3 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $836, price is now $627 per person
$627
per person
found 1 day ago
In convenient area either by walking or uber
Reviewed on Oct 18, 2025
Addison first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Felix River North/Magnificent Mile
8.2/10 Very Good! (2,575 reviews)
May 6 - May 11
5 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • FirstClass
Chicago (ORD) to Boston (BOS)
United • FirstClass
Price was $1,091, price is now $896 per person
$896
per person
found 15 hours ago
The rooms were clean and smelled fresh.
Reviewed on Jan 8, 2026
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (3,495 reviews)
May 6 - May 11
5 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • FirstClass
Chicago (ORD) to Boston (BOS)
United • FirstClass
Price was $1,563, price is now $1,085 per person
$1,085
per person
found 15 hours ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.
Reviewed on Jan 14, 2026
4.0-star property
Level Chicago - River North
9.2/10 Wonderful! (876 reviews)
May 6 - May 11
5 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • FirstClass
Chicago (ORD) to Boston (BOS)
United • FirstClass
Price was $1,289, price is now $1,042 per person
$1,042
per person
found 15 hours ago
The pool area is fantastic. Rooms very ample-sized and comfortable. I would stay here again!
Reviewed on Jul 8, 2024
More About Flying To Addison from Boston
Route Information for Flights from Boston to Addison
Origin Airport IATA Code | BOS |
|---|---|
Destination Airport IATA Code | CHI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Boston to Addison
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Addison Airports
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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.