$122 Cheap flight deals from San Francisco (SJC) to Addison (CHI)

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This Weekend's Flight Deals from San Francisco 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.

Sun, May 24 - Wed, May 27
SFO
San Francisco Intl.
MDW
Midway Intl.
$361 Roundtrip, found 1 day ago
$361
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 24 from San Francisco Intl. to Midway Intl., returning Wed, May 27, priced at $361 found 1 day ago
Sat, May 23 - Wed, May 27
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$371 Roundtrip, just found
$371
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 23 from San Francisco Intl. to O'Hare Intl., returning Wed, May 27, priced at $371 just found
Sat, May 23 - Wed, May 27
OAK
Oakland Intl.
ORD
O'Hare Intl.
$391 Roundtrip, found 5 days ago
$391
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Sat, May 23 from Oakland Intl. to O'Hare Intl., returning Wed, May 27, priced at $391 found 5 days ago
Sun, May 24 - Thu, May 28
OAK
Oakland Intl.
MDW
Midway Intl.
$393 Roundtrip, found 12 hours ago
$393
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Sun, May 24 from Oakland Intl. to Midway Intl., returning Thu, May 28, priced at $393 found 12 hours ago

Airfares from $122 One Way, $240 Round Trip from San Francisco to Addison

Prices starting at $240 for return flights and $122 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.

Thu, Oct 15 - Wed, Oct 21
SFO
San Francisco
ORD
Chicago
$240 Roundtrip, found 11 hours ago
$240
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Thu, Oct 15 from San Francisco to Chicago, returning Wed, Oct 21, priced at $240 found 11 hours ago
Wed, Sep 23 - Wed, Sep 30
SJC
San Jose
ORD
Chicago
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select United flight, departing Wed, Sep 23 from San Jose to Chicago, returning Wed, Sep 30, priced at $257 found 1 day ago
Wed, Oct 7 - Wed, Oct 14
SFO
San Francisco
MDW
Chicago
$257 Roundtrip, found 15 hours ago
$257
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, Oct 7 from San Francisco to Chicago, returning Wed, Oct 14, priced at $257 found 15 hours ago
Wed, Oct 21 - Wed, Oct 28
SFO
San Francisco
ORD
Chicago
$257 Roundtrip, found 15 hours ago
$257
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Wed, Oct 21 from San Francisco to Chicago, returning Wed, Oct 28, priced at $257 found 15 hours ago
Wed, Oct 21 - Wed, Oct 28
SFO
San Francisco
ORD
Chicago
$257 Roundtrip, found 15 hours ago
$257
Roundtrip
found 15 hours ago
Select United flight, departing Wed, Oct 21 from San Francisco to Chicago, returning Wed, Oct 28, priced at $257 found 15 hours ago

Addison economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,507 reviews)

Jun 21 - Jun 24

3 night stay

San Francisco (SFO) to Chicago (ORD)

United • Roundtrip • Coach
Price was $1,109, price is now $843 per person
$843
per person
found 1 day ago
Really nice property, rooms were clean, and staff was extremely friendly

Reviewed on May 5, 2026

Kimpton Gray Hotel by IHG
4.5-star property

Kimpton Gray Hotel by IHG

9.4/10 Exceptional! (1,008 reviews)

Jul 8 - Jul 12

4 night stay

San Francisco (SFO) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to San Francisco (SFO)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,348, price is now $969 per person
$969
per person
found 20 hours ago
I absolutely loved my stay at this property! Everything—from the warm, welcoming atmosphere to the beautifully maintained rooms—made the experience unforgettable. The staff were incredibly kind, and every detail felt thoughtfully designed for comfort. I can’t wait to come back!

Reviewed on Nov 21, 2025

Hotel Saint Clair- Magnificent Mile
4.0-star property

Hotel Saint Clair- Magnificent Mile

8.4/10 Very Good! (1,936 reviews)

Jun 20 - Jun 27

7 night stay

San Francisco (SFO) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to San Francisco (SFO)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,895, price is now $1,367 per person
$1,367
per person
found 1 day ago
The hotel needs to invest in a service elevator for their employees because there can only be five people on the elevator at a time and there’s 16 floors and it takes forever before you can catch an elevator. Also, the room set up. The beds are super close to the wall in entryway so it makes it awkward to navigate. They need to make an adjustment. The sinks are super small with no room to really lay out your toiletries if needed.. The thermostat in my room in particular did not work even though a worker came in and tried to reset it and it was 40° in the room was reading 69° with no heat. Nobody came during the entire weekend to change the bedsheets to give us change switch out the trash. There was also no ironing board or iron in our rooms. Photographed shows robes in the rooms. There are no robes in the room. Everything we needed every time we had to calm down for them to bring it up.

Reviewed on May 4, 2026

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More About Flying To Addison from San Francisco

Route Information for Flights from San Francisco to Addison

Origin Airport IATA Code
SJC
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

San Francisco to Addison

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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.