$107 Cheap flight deals from San Francisco (SJC) to Skokie (CHI)

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This Weekend's Flight Deals from San Francisco to Skokie

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, Jul 12 - Thu, Jul 16
SFO
San Francisco Intl.
MDW
Midway Intl.
$374 Roundtrip, found 5 days ago
$374
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Jul 12 from San Francisco Intl. to Midway Intl., returning Thu, Jul 16, priced at $374 found 5 days ago
Fri, Jul 10 - Tue, Jul 21
OAK
Oakland Intl.
ORD
O'Hare Intl.
$425 Roundtrip, found 2 days ago
$425
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Fri, Jul 10 from Oakland Intl. to O'Hare Intl., returning Tue, Jul 21, priced at $425 found 2 days ago
Sat, Jul 11 - Mon, Jul 20
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$441 Roundtrip, found 1 hour ago
$441
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jul 11 from San Francisco Intl. to O'Hare Intl., returning Mon, Jul 20, priced at $441 found 1 hour ago
Sun, Jul 12 - Thu, Jul 16
SJC
Norman Y. Mineta San Jose Intl.
ORD
O'Hare Intl.
$458 Roundtrip, found 16 hours ago
$458
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sun, Jul 12 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Thu, Jul 16, priced at $458 found 16 hours ago

Airfares from $107 One Way, $213 Round Trip from San Francisco to Skokie

Prices starting at $213 for return flights and $107 for one-way flights to Skokie 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, Aug 4 - Tue, Aug 11
SFO
San Francisco
ORD
Chicago
$213 Roundtrip, just found
$213
Roundtrip
just found
Select United flight, departing Tue, Aug 4 from San Francisco to Chicago, returning Tue, Aug 11, priced at $213 just found
Tue, Sep 29 - Thu, Oct 1
SFO
San Francisco
ORD
Chicago
$213 Roundtrip, found 1 hour ago
$213
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Sep 29 from San Francisco to Chicago, returning Thu, Oct 1, priced at $213 found 1 hour ago
Sat, Sep 12 - Wed, Sep 16
SFO
San Francisco
MDW
Chicago
$214 Roundtrip, found 1 hour ago
$214
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sat, Sep 12 from San Francisco to Chicago, returning Wed, Sep 16, priced at $214 found 1 hour ago
Mon, Aug 24 - Wed, Aug 26
OAK
Oakland
MDW
Chicago
$219 Roundtrip, found 4 hours ago
$219
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Mon, Aug 24 from Oakland to Chicago, returning Wed, Aug 26, priced at $219 found 4 hours ago
Tue, Sep 22 - Tue, Sep 29
SFO
San Francisco
RFD
Rockford
$237 Roundtrip, found 5 days ago
$237
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Sep 22 from San Francisco to Rockford, returning Tue, Sep 29, priced at $237 found 5 days ago

Skokie economy flight packages

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.6/10 Exceptional! (1,910 reviews)

Aug 27 - Aug 28

1 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Price was $768, price is now $641 per person
$641
per person
found 1 day ago
The best hotel we have ever stayed at!

Reviewed on Jul 6, 2026

Nobu Hotel Chicago
5.0-star property

Nobu Hotel Chicago

9.4/10 Exceptional! (879 reviews)

Aug 6 - Aug 8

2 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $1,080, price is now $859 per person
$859
per person
found 1 day ago
Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our stay here, though there are a few things to mention that made our stay less than a perfect 10. The bathroom is fully painted in black. Looks great, but terrible for styling your hair, if you have dark colored hair. Poor lighting concepts throughout the room and bathroom in general, which made it terrible for getting ready any time of the day. Closet area was dark, not great for getting dressed. Bedroom area was dark, not great for reading a book. Desk area is dark, not great for working remotely. Bathroom lighting is dark, not great if you are a woman trying to put on makeup. Housekeeping was fantastic and really knew how to personalize your stay, but they still knocked on the door when we had the "do not disturb" light on, which was very bothersome and woke us up a couple of times.

Reviewed on Jul 6, 2026

The Emily Hotel
4.0-star property

The Emily Hotel

9.2/10 Wonderful! (1,323 reviews)

Aug 8 - Aug 10

2 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Oakland (OAK)

Alaska Airlines • Coach
Price was $887, price is now $727 per person
$727
per person
found 1 day ago

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Skokie 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! (4,586 reviews)

Aug 17 - Aug 22

5 night stay

San Jose (SJC) to Chicago (ORD)

Frontier Airlines • Non-stop • FirstClass

Chicago (ORD) to San Jose (SJC)

Alaska Airlines • Non-stop • FirstClass
Price was $1,907, price is now $1,408 per person
$1,408
per person
found 1 day ago
Anderson should receive a gold star! So helpful, patient, and has such a great personality. The room was clean on arrival but I did notice housekeeping never cleaned our room during our stay and we had to ask for fresh hand towels every morning. Breakfast was standard and I would definitely like to see an ice machine or at least the juice in the dispenser be cold. The burgers from the bar were good but the pepperoni pizza was very disappointing especially for $22.

Reviewed on Jul 7, 2026

Level Chicago - River North
4.0-star property

Level Chicago - River North

9.2/10 Wonderful! (1,020 reviews)

Aug 17 - Aug 22

5 night stay

San Jose (SJC) to Chicago (ORD)

Frontier Airlines • Non-stop • FirstClass

Chicago (ORD) to San Jose (SJC)

Alaska Airlines • Non-stop • FirstClass
Price was $1,955, price is now $1,478 per person
$1,478
per person
found 1 day ago
There is a family lounge and pool and it was really helpful for us. (we have 2 kids bc7&4 yo) The spacious room with full kitchen is very comfortable as well. We have 2 negative points. One is location. It is located around River North but a little bit far from the busy area. So there are not so many places to eat around. Another one is the water pressure in the shower is very weak.

Reviewed on Jul 7, 2026

The Langham, Chicago
5.0-star property

The Langham, Chicago

9.8/10 Exceptional! (1,003 reviews)

Aug 17 - Aug 22

5 night stay

San Jose (SJC) to Chicago (ORD)

Frontier Airlines • Non-stop • FirstClass

Chicago (ORD) to San Jose (SJC)

Alaska Airlines • Non-stop • FirstClass
Price was $3,478, price is now $2,687 per person
$2,687
per person
found 1 day ago
Lux accommodations, great spa!

Reviewed on Jul 7, 2026

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More About Flying To Skokie from San Francisco

Route Information for Flights from San Francisco to Skokie

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

San Francisco to Skokie

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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.