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Flight Deals from San Francisco to Chicago from $89

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Stops

  • Nonstop
    from $178
  • Up to 1 stop
    $197
  • Up to 2 stops
    $260

Airlines

  • Alaska Airlines
    $178
  • American Airlines
    $268
  • Delta Air Lines
    $256
  • Frontier Airlines
    $217
  • Hawaiian Airlines
    $192
  • Sun Country Airlines
    $296
  • United Airlines
    $268
  • Virgin Atlantic
    $256

Cabin Class

  • Economy
    $178

Departure Airports

  • San Francisco International Airport
    $178

Arrival Airports

  • Chicago Midway Airport
    $217
  • Chicago O Hare Airport
    $178

Layover Airports

  • Bob Hope Airport
    $270
  • Dallas Fort Worth International Airport
    $319
  • Denver International Airport
    $267
  • Detroit Metropolitan Airport
    $256
  • Harry Reid International Airport
    $217
  • Hartsfield Jackson Atlanta International Airport
    $217
  • John Wayne Airport-Orange County Airport
    $260
  • Los Angeles International Airport
    $346
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $256
  • Phoenix Sky Harbor International Airport
    $267
  • Portland International Airport
    $216
  • Salt Lake City International Airport
    $256
  • Seattle Tacoma International Airport
    $197

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On average save $240 per traveler
Alaska Airlines Logo
Alaska Airlines

05/20/25

SFO
6h 26m
Direct

05/20/25

ORD
Alaska Airlines Logo
Alaska Airlines

05/24/25

ORD
2h 50m
Direct

05/24/25

SFO
$178
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/28/25

SFO
6h 26m
Direct

05/28/25

ORD
Alaska Airlines Logo
Alaska Airlines

05/29/25

ORD
2h 50m
Direct

05/29/25

SFO
$178
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/17/25

SFO
6h 26m
Direct

05/17/25

ORD
Hawaiian Airlines Logo
Hawaiian Airlines

05/24/25

ORD
2h 50m
Direct

05/24/25

SFO
$192
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/20/25

SFO
6h 26m
Direct

05/20/25

ORD
Hawaiian Airlines Logo
Hawaiian Airlines

05/24/25

ORD
2h 50m
Direct

05/24/25

SFO
$192
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/28/25

SFO
6h 26m
Direct

05/28/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/03/25

ORD
7h 36m
SEA

06/03/25

SFO
$197
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/17/25

SFO
6h 26m
Direct

05/17/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/11/25

ORD
7h 36m
SEA

06/11/25

SFO
$197
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

06/04/25

SFO
6h 26m
Direct

06/04/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/07/25

ORD
5h 10m
PDX

06/07/25

SFO
$216
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

06/02/25

SFO
6h 26m
Direct

06/02/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/07/25

ORD
5h 10m
PDX

06/07/25

SFO
$216
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/09/25

SFO
9h 11m
LAS

06/09/25

MDW
Frontier Airlines Logo
Frontier Airlines

06/10/25

MDW
13h 26m
ATL

06/10/25

SFO
$217
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/24/25

SFO
10h 41m
ATL

05/25/25

MDW
Frontier Airlines Logo
Frontier Airlines

05/30/25

MDW
5h 59m
LAS

05/30/25

SFO
$217
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/11/25

SFO
7h 55m
MSP

06/11/25

MDW
Delta Air Lines Logo
Delta Air Lines

06/11/25

MDW
6h 5m
SEA

06/12/25

SFO
$256
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/10/25

SFO
7h 52m
MSP

06/10/25

MDW
Delta Air Lines Logo
Delta Air Lines

06/12/25

MDW
4h 37m
SLC

06/12/25

SFO
$256
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/26/25

SFO
10h 40m
DTW

05/26/25

ORD
Delta Air Lines Logo
Delta Air Lines

06/03/25

ORD
5h 36m
SEA

06/03/25

SFO
$256
Free cancellation within 83 hours of booking
Virgin Atlantic Logo
Virgin Atlantic

05/30/25

SFO
7h 55m
SLC

05/30/25

ORD
Virgin Atlantic Logo
Virgin Atlantic

06/02/25

ORD
5h 6m
SLC

06/03/25

SFO
$256
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/02/25

SFO
7h 55m
SLC

06/02/25

ORD
Delta Air Lines Logo
Delta Air Lines

06/10/25

ORD
8h 44m
SEA

06/10/25

SFO
$256
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/25/25

SFO
9h 5m
ATL

05/25/25

MDW
Delta Air Lines Logo
Delta Air Lines

06/03/25

MDW
5h 48m
DTW

06/03/25

SFO
$256
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/19/25

SFO
8h 51m
SEA

05/20/25

ORD
Alaska Airlines Logo
Alaska Airlines

05/28/25

ORD
11h 22m
SEA
SNA

05/28/25

SFO
$260
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/19/25

SFO
7h 56m
MSP

05/19/25

MDW
Delta Air Lines Logo
Delta Air Lines

05/22/25

MDW
10h 4m
DTW
SLC

05/22/25

SFO
$261
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/16/25

SFO
8h 39m
PHX

05/16/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/19/25

ORD
6h 48m
DEN

05/20/25

SFO
$267
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/13/25

SFO
6h 19m
Direct

05/13/25

ORD
United Airlines Logo
United Airlines

05/21/25

ORD
2h 54m
Direct

05/21/25

SFO
$268
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

SFO
6h 33m
Direct

05/25/25

ORD
American Airlines Logo
American Airlines

05/28/25

ORD
2h 49m
Direct

05/28/25

SFO
$268
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/28/25

SFO
6h 33m
Direct

05/28/25

ORD
American Airlines Logo
American Airlines

05/31/25

ORD
2h 56m
Direct

05/31/25

SFO
$268
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/25/25

SFO
6h 20m
Direct

05/25/25

ORD
United Airlines Logo
United Airlines

05/28/25

ORD
2h 50m
Direct

05/28/25

SFO
$268
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/31/25

SFO
15h 25m
BUR
SEA

06/01/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/03/25

ORD
7h 43m
SEA

06/03/25

SFO
$270
Free cancellation within 83 hours of booking
Sun Country Airlines Logo
Sun Country Airlines

06/02/25

SFO
9h 45m
MSP

06/02/25

ORD
Sun Country Airlines Logo
Sun Country Airlines

06/09/25

ORD
4h 44m
MSP

06/09/25

SFO
$296
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/31/25

SFO
15h 25m
BUR
SEA

06/01/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/03/25

ORD
10h 25m
SEA
PDX

06/03/25

SFO
$314
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/04/25

SFO
10h 43m
PHX

06/05/25

ORD
American Airlines Logo
American Airlines

06/07/25

ORD
2h 39m
Direct

06/07/25

SFO
$316
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/15/25

SFO
12h 13m
ATL

05/16/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/18/25

ORD
8h 21m
DFW

05/18/25

SFO
$319
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/25/25

SFO
16h 56m
SEA
PDX

05/25/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/03/25

ORD
8h 58m
SEA
SNA

06/03/25

SFO
$339
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/04/25

SFO
9h 36m
LAX

06/04/25

ORD
American Airlines Logo
American Airlines

06/07/25

ORD
6h 36m
LAX

06/07/25

SFO
$346
Free cancellation within 83 hours of booking

Top Deals on flights from San Francisco to Chicago

San Francisco, US (SFO) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

May 17

SFO
6h 26m
Direct

May 17

ORD

as low as

$89

San Francisco, US (SFO) - Chicago, US (CHI)

Hawaiian Airlines Logo
Hawaiian Airlines

May 20

SFO
6h 26m
Direct

May 20

ORD

as low as

$96

San Francisco, US (SFO) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

May 24

SFO
10h 41m
ATL

May 25

MDW

as low as

$103

San Francisco, US (SFO) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

May 25

SFO
9h 15m
LAS

May 25

MDW

as low as

$113

San Francisco, US (SFO) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

May 30

SFO
11h 4m
DFW

May 31

ORD

as low as

$113

San Francisco, US (SFO) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

May 28

SFO
8h 54m
PDX

May 28

ORD

as low as

$118

San Francisco, US (SFO) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

Jun 11

SFO
11h 55m
SEA

Jun 11

ORD

as low as

$118

San Francisco, US (SFO) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

May 29

SFO
11h 11m
DEN

May 29

MDW

as low as

$119

San Francisco, US (SFO) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jun 7

SFO
10h 31m
DTW

Jun 7

MDW

as low as

$128

San Francisco, US (SFO) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jun 6

SFO
7h 55m
SLC

Jun 6

ORD

as low as

$128

San Francisco, US (SFO) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jun 11

SFO
7h 55m
MSP

Jun 11

MDW

as low as

$128

San Francisco, US (SFO) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

May 16

SFO
8h 39m
PHX

May 16

ORD

as low as

$133

Frequently Asked Questions

What is the typical flight duration from San Francisco to Chicago?
The typical direct flight from San Francisco to Chicago takes between 4 to 5 hours, depending on weather conditions and the specific flight path chosen. While your journey is generally consistent, variations might occur due to air traffic or runway usage. It is advisable to check your flight status closer to departure, as even minor delays can extend your travel time. Planning extra time for boarding and possible layovers ensures a smoother overall travel experience between these two major cities.
Are there any direct flights from San Francisco to Chicago?
Yes, there are direct flights available from San Francisco to Chicago. Major carriers like United Airlines and American Airlines frequently operate non-stop services, which typically range in frequency throughout the week. Direct flights are a faster option compared to itineraries with layovers, helping you reach your destination more efficiently. However, schedules can change seasonally and based on travel demand, so reviewing current flight availability and booking early can secure better fares and preferred flight times for your trip.
What are the best transportation options from Chicago airport to downtown?
Travelers arriving at Chicago’s airports have several efficient transportation options to reach downtown. One practical choice is the Blue Line train, which typically takes between 35 to 50 minutes with fares ranging from $5 to $10. Additionally, rideshare services and taxis offer door-to-door convenience with costs around $30 to $70, depending on traffic. Some hotels also provide shuttle services. Checking current fare estimates and schedules ahead of time will help you make an informed decision based on your travel itinerary and budget needs.
What are the must-see attractions in Chicago for travelers arriving from San Francisco?
Travelers should explore several key attractions during their visit. Highlights include Millennium Park, known for its iconic Cloud Gate sculpture, and the Art Institute of Chicago, which offers a rich collection of artworks. Navy Pier provides diverse dining and entertainment options, while a visit to Willis Tower Skydeck promises breathtaking city views. These sites provide a vibrant mix of culture, art, and urban exploration that differentiates this destination from San Francisco's landmarks.
Which local dishes should travelers from San Francisco try when visiting Chicago?
When exploring the local cuisine, visitors should sample Chicago-style deep-dish pizza and the renowned Chicago-style hot dogs, which are prepared with unique toppings and a distinctive style. Additionally, Italian beef sandwiches and Chicago’s diverse ethnic fare are must-tries. Restaurant prices typically range from $15 to $30 per meal, allowing you to explore both upscale dining and casual eateries with authentic flavors. Each dish offers a unique taste of the local culinary scene, providing a delicious contrast to the fare found in San Francisco.
Are there any family-friendly activities in Chicago for visitors from San Francisco?
Yes, there are numerous family-friendly activities available. Highlights include the interactive exhibits at the Museum of Science and Industry and the fascinating displays at the Shedd Aquarium. The Lincoln Park Zoo offers free admission and engaging outdoor activities. These options provide educational and entertaining experiences for all ages. Additionally, there are several parks and community events that cater to families, ensuring a fun and well-rounded visit that can appeal to the playful interests of visitors accustomed to the dynamic offerings in San Francisco.
What are the best budget-friendly hotels in Chicago for travelers from San Francisco?
Budget-conscious travelers can find several options in Chicago without compromising comfort. Many budget-friendly hotels and hostels in central locations offer rates between $100 to $200 per night. Establishments near public transit hubs like the Loop provide easy access to attractions. Options such as boutique inns and well-rated chain hotels often feature essential amenities, making them great bases for exploring culture and dining. It is wise to book in advance and check recent reviews to ensure that the chosen option aligns with your budget and travel expectations.
What are the top cultural experiences in Chicago that travelers from San Francisco should not miss?
Chicago offers an array of cultural experiences that stand out. Consider taking an architecture river cruise to appreciate the city’s famous skyline and historic structures, followed by a visit to the Art Institute of Chicago for its impressive art collections. The Theater District and live music venues provide additional cultural immersion. Exploring neighborhoods like Pilsen or Bronzeville can also reveal vibrant local arts and community stories. Each experience enriches your visit with a blend of history and modern creativity, offering a unique atmosphere distinct from San Francisco.
What are the safety tips for travelers from San Francisco visiting Chicago?
Safety remains a priority for visitors, so it’s recommended to stay aware of your surroundings, especially in crowded areas or when using public transit. Keep personal belongings secure and avoid isolated areas late at night. Use well-reviewed transportation services and follow local guidance. It also helps to have a working mobile phone and emergency contact details for local authorities. In case of unexpected situations, knowing the location of nearby police stations or tourist help centers can provide additional reassurance, ensuring your visit is as comfortable and safe as possible.
Is there a specific time of year when Chicago is best visited by travelers from San Francisco?
The optimal time to visit Chicago is generally during late spring to early fall. These months offer mild weather conditions, with temperatures typically ranging from 60°F to 80°F, making outdoor attractions and festivals very enjoyable. While summers can be lively with various events, spring and fall provide a balance between fewer crowds and pleasant temperatures. Winter visits might appeal to those who enjoy snowy cityscapes, though temperatures can drop significantly. Planning your trip during the shoulder seasons generally offers more comfortable sightseeing conditions.
What are the best places to shop for souvenirs in Chicago for travelers from San Francisco?
For a memorable shopping experience, consider visiting the Magnificent Mile, which hosts an array of specialty stores offering distinctive souvenirs. Navy Pier also has several boutiques featuring locally crafted items. Additionally, neighborhoods known for their art and vintage shops provide unique pieces that capture the essence of the city. Prices typically range from $10 to $100, giving you flexibility depending on your budget. Each venue offers a curated selection of items, ensuring a meaningful and self-expressive gift or memento from your trip.
What are the unique airport amenities in Chicago for travelers arriving from San Francisco?
Chicago airports offer a range of unique amenities aimed at enhancing your travel experience. At terminals like O’Hare and Midway, you can enjoy locally inspired dining options, art installations, and retail spaces that showcase regional products. Free Wi-Fi, comfortable lounges, and in some cases spa services provide added convenience. Some terminals even feature play areas for children and quiet zones for business travelers. These thoughtfully curated spaces help make the waiting time more productive and enjoyable, giving you a preview of the city’s vibrant culture before you venture into downtown.
Are there any seasonal events in Chicago that travelers from San Francisco should not miss?
Yes, Chicago hosts several seasonal events that are worth planning around. Summer brings the Chicago Air and Water Show and Taste of Chicago, offering dynamic cultural and culinary experiences. In the fall, festivals celebrating art, music, and local heritage add vibrancy to the cityscape. Winter features festive markets like the Christkindlmarket, creating a cozy atmosphere despite the cold. Each event provides an opportunity to immerse yourself in the city’s local traditions and vibrant community life, ensuring that your visit is enriched by unique seasonal celebrations.
What are the customs requirements for travelers flying from San Francisco to Chicago?
For domestic travel between San Francisco and Chicago, there are no customs requirements, as both cities are within the United States. However, all travelers must present a valid government-issued photo identification in accordance with TSA regulations. It’s also important to be aware of security screening procedures, carry-on restrictions, and any recent updates regarding travel guidelines. Preparing these documents and reviewing the Transportation Security Administration’s website ahead of your trip can help ensure a smooth and compliant experience at the airport.
What are the best solo travel activities in Chicago for travelers arriving from San Francisco?
Solo travelers in Chicago have a wide range of activities to enjoy. Consider exploring independent walking tours of the city’s architectural marvels, which typically run for 1 to 2 hours and provide in-depth historical insights. Visits to museums like the Art Institute or local galleries offer enriching experiences, often at reasonable admission prices ranging from $15 to $30. Additionally, participating in food tours or attending cultural events can facilitate meeting others while enjoying the city’s vibrant atmosphere. Such activities provide both personal enrichment and safe opportunities to immerse yourself in urban life.
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