$73 Cheap flight deals from San Francisco (SJC) to Countryside (CHI)

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This Weekend's Flight Deals from San Francisco to Countryside

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, Jan 11 - Sat, Jan 17
SFO
San Francisco Intl.
MDW
Midway Intl.
$266 Roundtrip, found 2 days ago
$266
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Jan 11 from San Francisco Intl. to Midway Intl., returning Sat, Jan 17, priced at $266 found 2 days ago
Sun, Jan 11 - Fri, Jan 16
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$334 Roundtrip, found 3 hours ago
$334
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, Jan 11 from San Francisco Intl. to O'Hare Intl., returning Fri, Jan 16, priced at $334 found 3 hours ago
Sun, Jan 11 - Sat, Jan 17
OAK
Oakland Intl.
MDW
Midway Intl.
$419 Roundtrip, found 2 days ago
$419
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Jan 11 from Oakland Intl. to Midway Intl., returning Sat, Jan 17, priced at $419 found 2 days ago
Sat, Jan 10 - Sat, Jan 17
SFO
San Francisco Intl.
RFD
Greater Rockford
$431 Roundtrip, found 3 days ago
$431
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jan 10 from San Francisco Intl. to Greater Rockford, returning Sat, Jan 17, priced at $431 found 3 days ago

Airfares from $73 One Way, $148 Round Trip from San Francisco to Countryside

Prices starting at $148 for return flights and $73 for one-way flights to Countryside were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Feb 10 - Wed, Feb 18
SFO
San Francisco
ORD
Chicago
$148 Roundtrip, found 1 day ago
$148
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Feb 10 from San Francisco to Chicago, returning Wed, Feb 18, priced at $148 found 1 day ago
Thu, Feb 5 - Mon, Feb 9
OAK
Oakland
ORD
Chicago
$161 Roundtrip, just found
$161
Roundtrip
just found
Select Alaska Airlines flight, departing Thu, Feb 5 from Oakland to Chicago, returning Mon, Feb 9, priced at $161 just found
Wed, Feb 18 - Mon, Feb 23
SFO
San Francisco
MDW
Chicago
$165 Roundtrip, found 2 days ago
$165
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Feb 18 from San Francisco to Chicago, returning Mon, Feb 23, priced at $165 found 2 days ago
Thu, Mar 5 - Mon, Mar 9
SJC
San Jose
ORD
Chicago
$179 Roundtrip, just found
$179
Roundtrip
just found
Select Alaska Airlines flight, departing Thu, Mar 5 from San Jose to Chicago, returning Mon, Mar 9, priced at $179 just found
Fri, Mar 6 - Tue, Mar 10
SFO
San Francisco
ORD
Chicago
$181 Roundtrip, just found
$181
Roundtrip
just found
Select Delta flight, departing Fri, Mar 6 from San Francisco to Chicago, returning Tue, Mar 10, priced at $181 just found

Countryside economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Feb 6 - Feb 8

2 night stay

San Francisco (SFO) to Chicago (ORD)

Alaska Airlines • Non-stop • Coach

Chicago (ORD) to San Francisco (SFO)

Frontier Airlines • Non-stop • Coach
Price was $470, price is now $380 per person
$380
per person
found 11 hours ago
Staff is TOP NOTCH! I am in a wheelchair right now, recovering from a knee surgery, and staff could not have been more solicitous and helpful. Also, when we checked in, upon learning of my daughter‘s birthday on Christmas, the front desk representative gave us a complementary room upgrade and sent up chocolates! The room was very clean and the shower was fantastic. Not enough good words about the buffet, as long as you’re clear that it is a “breakfast“ buffet and not a “brunch“ buffet :-). I think I was expecting a sliced roast beef and an omelette bar, but it is in fact a very extensive selection of breakfast foods. The restaurant recommendation was spot on. We had a delicious dinner of fine Mediterranean/Sardinian foodat Nora’s next door and enjoyed it immensely. I have now joined the capital RIU club and plan on spending much more time at their other properties, particularly in Costa Rica, where I am moving next month. Kudos to all, and thank you for our wonderful stay!

Reviewed on Dec 28, 2025

Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (2,008 reviews)

Feb 6 - Feb 8

2 night stay

San Francisco (SFO) to Chicago (ORD)

Alaska Airlines • Non-stop roundtrip • Coach
Price was $489, price is now $400 per person
$400
per person
found 10 hours ago
Solid place to stay

Reviewed on Nov 5, 2025

Motel Edgebrook Chicago North Shore by OYO
2.0-star property

Motel Edgebrook Chicago North Shore by OYO

6.2/10 (365 reviews)

Feb 17 - Feb 24

7 night stay

San Francisco (SFO) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to San Francisco (SFO)

Frontier Airlines • Coach
Price was $557, price is now $392 per person
$392
per person
found 1 hour ago
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More About Flying To Countryside from San Francisco

Route Information for Flights from San Francisco to Countryside

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

San Francisco to Countryside

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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.