$83 Cheap flight deals from San Francisco (SJC) to DeKalb (CHI)

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This Weekend's Flight Deals from San Francisco to DeKalb

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.

Fri, Apr 10 - Thu, Apr 16
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$320 Roundtrip, found 12 hours ago
$320
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Fri, Apr 10 from San Francisco Intl. to O'Hare Intl., returning Thu, Apr 16, priced at $320 found 12 hours ago
Fri, Apr 10 - Mon, Apr 13
SJC
Norman Y. Mineta San Jose Intl.
ORD
O'Hare Intl.
$464 Roundtrip, found 22 hours ago
$464
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Fri, Apr 10 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Mon, Apr 13, priced at $464 found 22 hours ago
Sun, Apr 12 - Wed, Apr 15
SFO
San Francisco Intl.
RFD
Greater Rockford
$496 Roundtrip, found 5 days ago
$496
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Apr 12 from San Francisco Intl. to Greater Rockford, returning Wed, Apr 15, priced at $496 found 5 days ago
Fri, Apr 10 - Sun, Apr 12
OAK
Oakland Intl.
ORD
O'Hare Intl.
$526 Roundtrip, found 1 day ago
$526
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Apr 10 from Oakland Intl. to O'Hare Intl., returning Sun, Apr 12, priced at $526 found 1 day ago

Airfares from $83 One Way, $163 Round Trip from San Francisco to DeKalb

Prices starting at $163 for return flights and $83 for one-way flights to DeKalb were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Apr 29 - Tue, May 5
SFO
San Francisco
ORD
Chicago
$163 Roundtrip, found 7 hours ago
$163
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Wed, Apr 29 from San Francisco to Chicago, returning Tue, May 5, priced at $163 found 7 hours ago
Mon, Apr 27 - Tue, May 5
SJC
San Jose
ORD
Chicago
$218 Roundtrip, found 12 hours ago
$218
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Mon, Apr 27 from San Jose to Chicago, returning Tue, May 5, priced at $218 found 12 hours ago
Tue, Jun 9 - Wed, Jun 10
SFO
San Francisco
ORD
Chicago
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jun 9 from San Francisco to Chicago, returning Wed, Jun 10, priced at $237 found 2 days ago
Wed, Jun 3 - Sat, Jun 6
SJC
San Jose
ORD
Chicago
$247 Roundtrip, found 2 days ago
$247
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Wed, Jun 3 from San Jose to Chicago, returning Sat, Jun 6, priced at $247 found 2 days ago
Wed, May 13 - Sat, May 16
SFO
San Francisco
ORD
Chicago
$256 Roundtrip, found 5 hours ago
$256
Roundtrip
found 5 hours ago
Select United flight, departing Wed, May 13 from San Francisco to Chicago, returning Sat, May 16, priced at $256 found 5 hours ago

DeKalb 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! (3,688 reviews)

May 19 - May 22

3 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Price was $820, price is now $582 per person
$582
per person
found 2 hours 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

Sentral Michigan Avenue
4.0-star property

Sentral Michigan Avenue

9.2/10 Wonderful! (1,103 reviews)

May 6 - May 11

5 night stay

San Francisco (SFO) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to San Francisco (SFO)

Frontier Airlines • Coach
Price was $1,087, price is now $889 per person
$889
per person
found 1 day ago
Everything was perfect I will be back in Chicago and will use you guys all the time. Thank you for making my stay amazing and so cozy.

Reviewed on Nov 22, 2025

Eurostars Magnificent Mile
4.0-star property

Eurostars Magnificent Mile

9/10 Wonderful! (3,357 reviews)

May 22 - May 24

2 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Oakland (OAK)

Delta • Coach
Price was $883, price is now $680 per person
$680
per person
found 1 day ago
In convenient area either by walking or uber

Reviewed on Oct 18, 2025

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DeKalb packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
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! (2,401 reviews)

May 6 - May 11

5 night stay

San Francisco (SFO) to Chicago (ORD)

United • Roundtrip • PremiumEconomy
Price was $2,577, price is now $1,890 per person
$1,890
per person
found 18 hours ago
Courteous staff, clean room, conveniently located right on the pier.

Reviewed on Nov 3, 2025

Waldorf Astoria Chicago
5.0-star property

Waldorf Astoria Chicago

9.4/10 Exceptional! (1,002 reviews)

May 6 - May 11

5 night stay

San Francisco (SFO) to Chicago (ORD)

United • Roundtrip • PremiumEconomy
Price was $3,047, price is now $2,534 per person
$2,534
per person
found 18 hours 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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More About Flying To DeKalb from San Francisco

Route Information for Flights from San Francisco to DeKalb

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

San Francisco to DeKalb

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We make it as easy as possible for you to book great deals on flights from San Francisco to DeKalb. You won’t be forced to compromise on your schedule—you can pick San Francisco to DeKalb flights that suit your needs.

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.