$75 Cheap flight deals from San Francisco (SJC) to Des Plaines (CHI)

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This Weekend's Flight Deals from San Francisco to Des Plaines

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 18 - Tue, Feb 3
OAK
Oakland Intl.
MDW
Midway Intl.
$416 Roundtrip, found 3 days ago
$416
Roundtrip
found 3 days ago
Select Delta flight, departing Sun, Jan 18 from Oakland Intl. to Midway Intl., returning Tue, Feb 3, priced at $416 found 3 days ago
Sun, Jan 18 - Sun, Feb 1
OAK
Oakland Intl.
ORD
O'Hare Intl.
$420 Roundtrip, found 3 days ago
$420
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Sun, Jan 18 from Oakland Intl. to O'Hare Intl., returning Sun, Feb 1, priced at $420 found 3 days ago
Sun, Jan 18 - Sun, Feb 1
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$618 Roundtrip, found 2 hours ago
$618
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Sun, Jan 18 from San Francisco Intl. to O'Hare Intl., returning Sun, Feb 1, priced at $618 found 2 hours ago
Sat, Jan 17 - Mon, Jan 26
SFO
San Francisco Intl.
MDW
Midway Intl.
$677 Roundtrip, found 1 day ago
$677
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jan 17 from San Francisco Intl. to Midway Intl., returning Mon, Jan 26, priced at $677 found 1 day ago

Airfares from $75 One Way, $148 Round Trip from San Francisco to Des Plaines

Prices starting at $148 for return flights and $75 for one-way flights to Des Plaines 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
Tue, Mar 31 - Tue, Apr 7
OAK
Oakland
ORD
Chicago
$159 Roundtrip, found 6 days ago
$159
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Tue, Mar 31 from Oakland to Chicago, returning Tue, Apr 7, priced at $159 found 6 days ago
Sat, May 2 - Tue, May 5
SFO
San Francisco
ORD
Chicago
$160 Roundtrip, found 6 days ago
$160
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Sat, May 2 from San Francisco to Chicago, returning Tue, May 5, priced at $160 found 6 days ago
Wed, Feb 11 - Thu, Feb 19
SFO
San Francisco
MDW
Chicago
$170 Roundtrip, found 2 days ago
$170
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Feb 11 from San Francisco to Chicago, returning Thu, Feb 19, priced at $170 found 2 days ago
Mon, Apr 6 - Wed, Apr 15
SJC
San Jose
ORD
Chicago
$173 Roundtrip, found 6 days ago
$173
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Mon, Apr 6 from San Jose to Chicago, returning Wed, Apr 15, priced at $173 found 6 days ago

Des Plaines 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)

Mar 14 - Mar 16

2 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Price was $717, price is now $519 per person
$519
per person
found 1 hour ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (2,008 reviews)

Feb 26 - Mar 1

3 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Non-stop • Coach

Chicago (ORD) to Oakland (OAK)

Alaska Airlines • Non-stop • Coach
Price was $777, price is now $625 per person
$625
per person
found 1 day ago
Solid place to stay

Reviewed on Nov 5, 2025

Waldorf Astoria Chicago
5.0-star property

Waldorf Astoria Chicago

9.4/10 Exceptional! (1,000 reviews)

Mar 6 - Mar 9

3 night stay

San Francisco (SFO) to Chicago (ORD)

Delta • Non-stop • Coach

Chicago (ORD) to San Francisco (SFO)

Frontier Airlines • Non-stop • Coach
Price was $1,224, price is now $991 per person
$991
per person
found 1 day ago
Lovely room and spacious bathroom plus all of the high end touches (robes, slippers to soft mats and towels and great bath products and loved the nespresso maker!) View was not great but gym and lobby made up for it; bar was too crowded and we couldn’t get a late checkout but at least it was noon and they held our bags for a few hours!

Reviewed on Dec 31, 2025

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Des Plaines first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport
4.0-star property

Hilton Chicago O'Hare Airport

8.2/10 Very Good! (2,158 reviews)

Feb 26 - Feb 28

2 night stay

San Francisco (SFO) to Chicago (ORD)

Delta • Non-stop • FirstClass

Chicago (ORD) to San Francisco (SFO)

American Airlines • Non-stop • FirstClass
Price was $1,203, price is now $1,115 per person
$1,115
per person
found 1 day ago
Awesome hotel, an island of peace and calm and first class treatment in a sea of chaos at O'Hare airport. Staff, restaurant, services--worth every penny. Early departure? Stay here the night before. We did. Calmly woke up and walked to the terminal thru the underground walkways. Truly pleasant and memorable stay.

Reviewed on Nov 11, 2025

Chicago Marriott Suites Deerfield
4.0-star property

Chicago Marriott Suites Deerfield

8.6/10 Excellent! (1,000 reviews)

Feb 26 - Feb 28

2 night stay

San Francisco (SFO) to Chicago (ORD)

Delta • Non-stop • FirstClass

Chicago (ORD) to San Francisco (SFO)

American Airlines • Non-stop • FirstClass
Price was $1,270, price is now $1,162 per person
$1,162
per person
found 1 day ago
Staff was very nice and let me in my room early. Room was so nice and clean. It was a pleasure to there. Wish all hotels were like this one.

Reviewed on Jul 20, 2025

Hilton Rosemont Chicago O'Hare
3.5-star property

Hilton Rosemont Chicago O'Hare

8.4/10 Very Good! (1,000 reviews)

Feb 26 - Feb 28

2 night stay

San Francisco (SFO) to Chicago (ORD)

Delta • Non-stop • FirstClass

Chicago (ORD) to San Francisco (SFO)

American Airlines • Non-stop • FirstClass
Price was $1,245, price is now $1,149 per person
$1,149
per person
found 1 day ago
Good hotel close to airport, with free airport shuttle, 7-10 min away. Quite convenient

Reviewed on Nov 4, 2025

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More About Flying To Des Plaines from San Francisco

Route Information for Flights from San Francisco to Des Plaines

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

San Francisco to Des Plaines

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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.