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

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This Weekend's Flight Deals from San Francisco to West Side

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 18 - Sat, May 24
SFO
San Francisco Intl.
MDW
Midway Intl.
$222 Roundtrip, found 2 hours ago
$222
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, May 18 from San Francisco Intl. to Midway Intl., returning Sat, May 24, priced at $222 found 2 hours ago
Fri, May 16 - Sat, May 24
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$282 Roundtrip, just found
$282
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 16 from San Francisco Intl. to O'Hare Intl., returning Sat, May 24, priced at $282 just found
Sun, May 18 - Wed, May 21
SJC
Norman Y. Mineta San Jose Intl.
ORD
O'Hare Intl.
$303 Roundtrip, found 4 hours ago
$303
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sun, May 18 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Wed, May 21, priced at $303 found 4 hours ago
Fri, May 16 - Mon, May 19
OAK
Oakland Intl.
MDW
Midway Intl.
$376 Roundtrip, found 3 days ago
$376
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, May 16 from Oakland Intl. to Midway Intl., returning Mon, May 19, priced at $376 found 3 days ago

Airfares from $73 One Way, $126 Round Trip from San Francisco to West Side

Prices starting at $126 for return flights and $73 for one-way flights to West Side 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, May 31 - Tue, Jun 3
OAK
Oakland
ORD
Chicago
$126 Roundtrip, found 4 days ago
$126
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, May 31 from Oakland to Chicago, returning Tue, Jun 3, priced at $126 found 4 days ago
Wed, May 28 - Thu, Jun 5
SJC
San Jose
ORD
Chicago
$132 Roundtrip, found 4 days ago
$132
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, May 28 from San Jose to Chicago, returning Thu, Jun 5, priced at $132 found 4 days ago
Tue, May 27 - Thu, Jun 5
SFO
San Francisco
ORD
Chicago
$143 Roundtrip, found 5 days ago
$143
Roundtrip
found 5 days ago
Select United flight, departing Tue, May 27 from San Francisco to Chicago, returning Thu, Jun 5, priced at $143 found 5 days ago
Mon, Jul 28 - Mon, Aug 18
SFO
San Francisco
ORD
Chicago
$149 Roundtrip, found 4 days ago
$149
Roundtrip
found 4 days ago
Select United flight, departing Mon, Jul 28 from San Francisco to Chicago, returning Mon, Aug 18, priced at $149 found 4 days ago
Sat, May 24 - Thu, May 29
SFO
San Francisco
MDW
Chicago
$171 Roundtrip, found 5 days ago
$171
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 24 from San Francisco to Chicago, returning Thu, May 29, priced at $171 found 5 days ago

West Side economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Buckingham Hotel
3.5-star property

The Buckingham Hotel

9/10 Wonderful! (1,001 reviews)

Jun 24 - Jun 29

5 night stay

San Francisco (SFO) to Chicago (ORD)

United • Coach

Chicago (ORD) to San Francisco (SFO)

Alaska Airlines • Coach
Save 100% on your flight
per person
found 17 hours ago
There was no internet, no charging docs that worked, no music. And then when we tried to go out for the evening they were doing maintenance and wouldn’t let us leave the property so we lost our reservations. It was a beautiful room but terrible unexpected troubles.

Reviewed on Mar 9, 2023

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (295 reviews)

Jun 17 - Jun 22

5 night stay

San Francisco (SFO) to Chicago (ORD)

United • Coach

Chicago (ORD) to San Francisco (SFO)

American Airlines • Coach
Save 100% on your flight
per person
found 18 hours ago
Front desk and maintenance staff was amazing super succeeded our expectations i will return gor future dates

Reviewed on Feb 16, 2024

Level Chicago - River North
4.0-star property

Level Chicago - River North

9/10 Wonderful! (501 reviews)

Jun 24 - Jun 29

5 night stay

San Francisco (SFO) to Chicago (ORD)

United • Coach

Chicago (ORD) to San Francisco (SFO)

Alaska Airlines • Coach
Save 100% on your flight
per person
found 17 hours ago
The pool area is fantastic. Rooms very ample-sized and comfortable. I would stay here again!

Reviewed on Jul 8, 2024

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More About Flying To West Side from San Francisco

Route Information for Flights from San Francisco to West Side

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

San Francisco to West Side

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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.