$79 Cheap flight deals from San Francisco (SJC) to Countryside (CHI)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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.

Sat, Aug 22 - Tue, Aug 25
SFO
San Francisco Intl.
MDW
Midway Intl.
$338 Roundtrip, found 21 hours ago
$338
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Sat, Aug 22 from San Francisco Intl. to Midway Intl., returning Tue, Aug 25, priced at $338 found 21 hours ago
Sun, Aug 23 - Wed, Aug 26
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$343 Roundtrip, just found
$343
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Aug 23 from San Francisco Intl. to O'Hare Intl., returning Wed, Aug 26, priced at $343 just found
Sat, Aug 22 - Sat, Sep 5
OAK
Oakland Intl.
ORD
O'Hare Intl.
$378 Roundtrip, found 2 days ago
$378
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sat, Aug 22 from Oakland Intl. to O'Hare Intl., returning Sat, Sep 5, priced at $378 found 2 days ago
Sun, Aug 23 - Fri, Sep 4
SJC
Norman Y. Mineta San Jose Intl.
ORD
O'Hare Intl.
$475 Roundtrip, found 17 hours ago
$475
Roundtrip
found 17 hours ago
Select Bargain Flight flight, departing Sun, Aug 23 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Fri, Sep 4, priced at $475 found 17 hours ago

Airfares from $79 One Way, $158 Round Trip from San Francisco to Countryside

Prices starting at $158 for return flights and $79 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.

Sat, Sep 26 - Mon, Sep 28
SFO
San Francisco
MDW
Chicago
$158 Roundtrip, just found
$158
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Sep 26 from San Francisco to Chicago, returning Mon, Sep 28, priced at $158 just found
Thu, Oct 1 - Thu, Oct 15
SJC
San Jose
ORD
Chicago
$158 Roundtrip, found 15 hours ago
$158
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Thu, Oct 1 from San Jose to Chicago, returning Thu, Oct 15, priced at $158 found 15 hours ago
Thu, Sep 17 - Mon, Sep 21
OAK
Oakland
ORD
Chicago
$158 Roundtrip, found 17 hours ago
$158
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Sep 17 from Oakland to Chicago, returning Mon, Sep 21, priced at $158 found 17 hours ago
Mon, Sep 21 - Thu, Sep 24
SFO
San Francisco
ORD
Chicago
$158 Roundtrip, just found
$158
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Sep 21 from San Francisco to Chicago, returning Thu, Sep 24, priced at $158 just found
Tue, Sep 8 - Sat, Sep 12
SFO
San Francisco
RFD
Rockford
$219 Roundtrip, found 4 days ago
$219
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Sep 8 from San Francisco to Rockford, returning Sat, Sep 12, priced at $219 found 4 days ago

Countryside economy flight packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (512 reviews)

Oct 13 - Oct 17

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 $1,061, price is now $736 per person
$736
per person
found 1 day ago
The property seems new and well kept. There are many amenities that enhance the stay including a pool, hot tub, basketball ball court, game room, sauna and steam room. We loved our stay. Only negatives were there was not an ice machine, there was not daily cleaning service, the towels were OK and we needed our trash emptied but were many sure how to request that. Overall a great spot. Affordable and lots of space with great views!

Reviewed on Aug 15, 2026

Level Chicago - River North
4.0-star property

Level Chicago - River North

9.2/10 Wonderful! (1,043 reviews)

Oct 9 - Oct 12

3 night stay

San Francisco (SFO) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,833, price is now $1,179 per person
$1,179
per person
found 1 day ago
Nice neat clean room. It was a lot community so you felt safe.

Reviewed on Aug 18, 2026

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! (2,638 reviews)

Oct 3 - Oct 6

3 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,260, price is now $905 per person
$905
per person
found 9 hours ago
Loved the location. Was able to park in the parking ramp, leave the car, and walk to many, many places! Room was clean, view was excellent, and choices of food/snacks was endless!

Reviewed on Aug 18, 2026

Don't see what you're looking for?
See all available trips from San Francisco to Countryside
View all trips

Countryside first class 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! (4,907 reviews)

Sep 21 - Sep 24

3 night stay

San Jose (SJC) to Chicago (ORD)

Delta • Non-stop roundtrip • FirstClass
Price was $2,048, price is now $1,699 per person
$1,699
per person
found 1 day ago
Great location. Nice hotel

Reviewed on Aug 18, 2026

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! (2,638 reviews)

Sep 21 - Sep 24

3 night stay

San Jose (SJC) to Chicago (ORD)

Delta • Non-stop roundtrip • FirstClass
Price was $2,220, price is now $1,843 per person
$1,843
per person
found 1 day ago
Loved the location. Was able to park in the parking ramp, leave the car, and walk to many, many places! Room was clean, view was excellent, and choices of food/snacks was endless!

Reviewed on Aug 18, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.6/10 Exceptional! (1,960 reviews)

Sep 21 - Sep 24

3 night stay

San Jose (SJC) to Chicago (ORD)

Delta • Non-stop roundtrip • FirstClass
Price was $2,350, price is now $2,010 per person
$2,010
per person
found 1 day ago

Don't see what you're looking for?
See all available trips from San Francisco to Countryside
View all trips

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

If you are looking to get guaranteed low prices for San Francisco to Countryside flights then Orbitz is the place to go. We use cutting edge mobile tools to find the best deals on air tickets and to keep you updated on delays and changes.

Get Package Savings by Booking Flights and Hotels at the Same Time

Using the Orbitz Matrix display, you can see how much you will save on flights from San Francisco to Countryside if the discount fare is combined with a hotel. You can also look at hotel reviews, photos and maps of the area, so it will be convenient to make your budget travel plans.

Orbitz for Business Helps Corporations save Money

Orbitz can assist all businesses from the small to major corporations with discounts on flights from San Francisco to Countryside. We fine- tune your needs for San Francisco to Countryside flights and optimize your plans by assessing your business and coming up with ways for you to save on air tickets.

Using Online Check-In Makes Flying Simple

You can use the Orbitz website to check-in for your flights from San Francisco to Countryside. You can also make changes to your schedule or even cancel a flight.

More Destinations

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.