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Flight Deals from San Diego to Chicago O Hare Airport from $73

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Stops

  • Nonstop
    from $157
  • Up to 1 stop
    $214

Airlines

  • Alaska Airlines
    $295
  • American Airlines
    $326
  • Delta Air Lines
    $322
  • Frontier Airlines
    $157
  • Hawaiian Airlines
    $337
  • Spirit Airlines
    $214
  • Sun Country Airlines
    $356
  • United Airlines
    $326

Cabin Class

  • Economy
    $157

Departure Airports

  • Mc Clellan-Palomar Airport
    $327
  • San Diego International Airport
    $157

Arrival Airports

  • Chicago O Hare Airport
    $157

Layover Airports

  • Dallas Fort Worth International Airport
    $264
  • Denver International Airport
    $358
  • Detroit Metropolitan Airport
    $337
  • George Bush Intercontinental Houston Airport
    $366
  • Harry Reid International Airport
    $214
  • Hartsfield Jackson Atlanta International Airport
    $333
  • Los Angeles International Airport
    $366
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $333
  • Phoenix Sky Harbor International Airport
    $327
  • Portland International Airport
    $314
  • Salt Lake City International Airport
    $322
  • San Francisco International Airport
    $337
  • Seattle Tacoma International Airport
    $295

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

06/24/25

SAN
6h 3m
Direct

06/24/25

ORD
Frontier Airlines Logo
Frontier Airlines

07/01/25

ORD
2h 12m
Direct

07/01/25

SAN
$157
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/25/25

SAN
6h 3m
Direct

06/25/25

ORD
Frontier Airlines Logo
Frontier Airlines

07/01/25

ORD
2h 12m
Direct

07/01/25

SAN
$170
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

06/11/25

SAN
9h 24m
LAS

06/12/25

ORD
Spirit Airlines Logo
Spirit Airlines

06/18/25

ORD
6h 36m
LAS

06/18/25

SAN
$214
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

06/18/25

SAN
10h 41m
LAS

06/19/25

ORD
Spirit Airlines Logo
Spirit Airlines

06/25/25

ORD
6h 36m
LAS

06/25/25

SAN
$214
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/16/25

SAN
6h 3m
Direct

06/16/25

ORD
Frontier Airlines Logo
Frontier Airlines

06/24/25

ORD
4h 56m
DFW

06/24/25

SAN
$264
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/27/25

SAN
6h 3m
Direct

06/27/25

ORD
Frontier Airlines Logo
Frontier Airlines

07/01/25

ORD
4h 56m
DFW

07/01/25

SAN
$289
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

06/09/25

SAN
12h 41m
SEA

06/10/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/17/25

ORD
8h 50m
SEA

06/17/25

SAN
$295
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

06/10/25

SAN
9h 53m
PDX

06/10/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/16/25

ORD
17h 59m
SEA

06/16/25

SAN
$314
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/11/25

SAN
10h 6m
SEA

06/12/25

ORD
Delta Air Lines Logo
Delta Air Lines

06/18/25

ORD
4h 24m
SLC

06/18/25

SAN
$322
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/01/25

SAN
6h 17m
Direct

07/01/25

ORD
American Airlines Logo
American Airlines

07/09/25

ORD
2h 15m
Direct

07/09/25

SAN
$326
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/10/25

SAN
6h 25m
Direct

06/10/25

ORD
American Airlines Logo
American Airlines

06/21/25

ORD
2h 20m
Direct

06/21/25

SAN
$326
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/11/25

SAN
6h 15m
Direct

06/11/25

ORD
United Airlines Logo
United Airlines

06/18/25

ORD
2h 23m
Direct

06/18/25

SAN
$326
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/09/25

SAN
6h 15m
Direct

07/09/25

ORD
United Airlines Logo
United Airlines

07/15/25

ORD
2h 28m
Direct

07/15/25

SAN
$326
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/28/25

SAN
6h 7m
Direct

06/29/25

ORD
American Airlines Logo
American Airlines

07/01/25

ORD
7h 2m
PHX

07/01/25

SAN
$327
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/10/25

CLD
9h 59m
PHX

06/10/25

ORD
American Airlines Logo
American Airlines

06/21/25

ORD
2h 20m
Direct

06/21/25

CLD
$327
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/24/25

SAN
8h 39m
SLC

06/24/25

ORD
Delta Air Lines Logo
Delta Air Lines

07/01/25

ORD
6h 15m
ATL

07/01/25

SAN
$333
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/25/25

SAN
8h 39m
SLC

06/25/25

ORD
Delta Air Lines Logo
Delta Air Lines

07/02/25

ORD
6h 49m
MSP

07/02/25

SAN
$333
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

07/01/25

SAN
8h 39m
SLC

07/01/25

ORD
Delta Air Lines Logo
Delta Air Lines

07/09/25

ORD
4h 51m
DTW

07/09/25

SAN
$337
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

06/24/25

SAN
11h 49m
SEA

06/25/25

ORD
Hawaiian Airlines Logo
Hawaiian Airlines

07/11/25

ORD
13h 44m
SFO

07/12/25

SAN
$337
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/15/25

SAN
11h 43m
DTW

06/15/25

ORD
Delta Air Lines Logo
Delta Air Lines

06/24/25

ORD
6h 49m
MSP

06/24/25

SAN
$353
Free cancellation within 83 hours of booking
Sun Country Airlines Logo
Sun Country Airlines

06/26/25

SAN
22h 56m
MSP

06/27/25

ORD
Sun Country Airlines Logo
Sun Country Airlines

06/30/25

ORD
22h 44m
MSP

07/01/25

SAN
$356
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/26/25

SAN
10h 59m
ATL

06/27/25

ORD
Delta Air Lines Logo
Delta Air Lines

06/30/25

ORD
6h 25m
ATL

06/30/25

SAN
$356
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

06/28/25

SAN
6h 3m
Direct

06/28/25

ORD
Frontier Airlines Logo
Frontier Airlines

07/05/25

ORD
4h 8m
DEN

07/05/25

SAN
$358
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

07/03/25

SAN
6h 3m
Direct

07/03/25

ORD
Frontier Airlines Logo
Frontier Airlines

07/10/25

ORD
4h 12m
DEN

07/10/25

SAN
$359
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

06/17/25

SAN
10h 42m
SEA

06/17/25

ORD
Hawaiian Airlines Logo
Hawaiian Airlines

06/24/25

ORD
8h 50m
SEA

06/24/25

SAN
$363
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

06/10/25

SAN
9h 53m
PDX

06/10/25

ORD
Hawaiian Airlines Logo
Hawaiian Airlines

06/16/25

ORD
8h 50m
SEA

06/16/25

SAN
$364
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/02/25

SAN
10h 12m
SFO

07/03/25

ORD
United Airlines Logo
United Airlines

07/09/25

ORD
2h 24m
Direct

07/09/25

SAN
$366
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/25/25

SAN
6h 15m
Direct

06/25/25

ORD
United Airlines Logo
United Airlines

07/02/25

ORD
5h 35m
IAH

07/02/25

SAN
$366
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/24/25

SAN
6h 15m
Direct

06/24/25

ORD
United Airlines Logo
United Airlines

07/01/25

ORD
6h 54m
LAX

07/01/25

SAN
$366
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/01/25

SAN
8h 50m
IAH

07/02/25

ORD
United Airlines Logo
United Airlines

07/09/25

ORD
2h 22m
Direct

07/09/25

SAN
$366
Free cancellation within 83 hours of booking

Top Deals on flights from San Diego to Chicago O Hare Airport

San Diego, US (SAN) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Jun 14

SAN
6h 3m
Direct

Jun 14

ORD

as low as

$73

San Diego, US (SAN) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

May 29

SAN
8h 11m
LAS

May 29

ORD

as low as

$93

San Diego, US (SAN) - Chicago, US (CHI)

Spirit Airlines Logo
Spirit Airlines

May 28

SAN
8h 37m
LAS

May 29

ORD

as low as

$97

San Diego, US (SAN) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

Jun 4

SAN
9h 53m
PDX

Jun 4

ORD

as low as

$128

San Diego, US (SAN) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

May 25

SAN
12h 44m
SFO

May 25

ORD

as low as

$136

San Diego, US (SAN) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Jun 6

SAN
11h 30m
PHX

Jun 6

ORD

as low as

$139

San Diego, US (SAN) - Chicago, US (CHI)

Hawaiian Airlines Logo
Hawaiian Airlines

Jun 4

SAN
9h 53m
PDX

Jun 4

ORD

as low as

$142

San Diego, US (SAN) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 24

SAN
10h 4m
SEA

May 24

ORD

as low as

$147

San Diego, US (SAN) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 31

SAN
6h 19m
Direct

May 31

ORD

as low as

$163

San Diego, US (SAN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jun 14

SAN
6h 7m
Direct

Jun 15

ORD

as low as

$163

San Diego, US (SAN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jun 10

CLD
8h 25m
PHX

Jun 10

ORD

as low as

$168

San Diego, US (SAN) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Jun 10

SAN
9h 4m
DFW

Jun 10

ORD

as low as

$173

Frequently Asked Questions

What is the typical flight duration from San Diego to Chicago O Hare Airport?
The typical flight duration from San Diego to Chicago O Hare Airport usually takes between 3 to 4 hours, although this can vary based on wind speeds and routing changes. Travelers flying from San Diego should be prepared for a moderately long journey, with most direct flights falling within this estimated time frame. Always check for the most up-to-date schedules at the time of your booking, as seasonal variations or slight delays may affect overall travel times.
Are there any direct flights from San Diego to Chicago O Hare Airport?
Yes, there are direct flights from San Diego to Chicago O Hare Airport, though availability may fluctuate based on the season and airline schedules. Direct services typically offer a smoother travel experience with fewer layovers, saving time for those traveling between these cities. It is advisable to check with various carriers for the most convenient departure times and competitive pricing, which often ranges between $150 to $400 one-way depending on the booking time and season.
What are the best transportation options from Chicago O Hare Airport to downtown Chicago?
The best transportation from Chicago O Hare Airport to downtown Chicago includes several convenient options. Travelers can opt for the CTA Blue Line, which offers an affordable journey with fares typically between $5 to $10, or choose ride-sharing services like Uber or Lyft, where costs can range from $30 to $50. Additionally, taxis and shuttle services are available, providing direct access to city landmarks while factoring in variable traffic conditions. Each method provides reliable access to downtown attractions from the airport.
What are the must-see attractions in Chicago for travelers arriving from San Diego?
Travelers arriving from San Diego should not miss Chicago’s iconic landmarks. The Millennium Park, home to the famous Cloud Gate sculpture, and the Willis Tower’s Skydeck offer breathtaking views of the skyline. Other attractions include Navy Pier, the Art Institute of Chicago, and Lincoln Park Zoo. These sites provide insights into the city’s rich cultural heritage and modern energy. Exploring these areas gives a comprehensive experience mixing scenic urban views with historical depth and interactive cultural activities.
Which local dishes should travelers from San Diego try when visiting Chicago?
Visitors from San Diego are encouraged to try Chicago’s local culinary specialties. The city is renowned for its deep-dish pizza, a hearty meal that differs greatly from California’s light fare, and Italian beef sandwiches known for their juicy flavor. Additionally, exploring Chicago-style hot dogs with their unique toppings offers a distinctive taste. These dishes provide a flavorful insight into Chicago’s vibrant food scene, combining traditional recipes with modern twists. Pair your meal with a local craft beer for an authentic dining experience.
Are there any family-friendly activities in Chicago for visitors from San Diego?
Yes, Chicago offers a wide range of family-friendly activities ideal for visitors coming from San Diego. Popular attractions include the interactive exhibits at the Field Museum and the engaging displays at the Museum of Science and Industry. Families can also enjoy outdoor time at Millennium Park, or take a leisurely boat tour along the Chicago River. In addition, the Lincoln Park Zoo and the Shedd Aquarium provide fun, educational experiences for all ages. These activities ensure that every family member enjoys an engaging, memorable visit.
What are the best budget-friendly hotels in Chicago for travelers from San Diego?
For those traveling from San Diego on a budget, Chicago offers a variety of affordable accommodations. Budget-friendly options such as the Holiday Inn Express, Hampton Inn, and boutique motels in areas like the Loop or near the Magnificent Mile often range from $100 to $200 per night. These hotels offer comfortable amenities, convenient access to public transportation, and proximity to major attractions. It is advisable to book in advance and compare prices across different platforms to secure the best deal during peak tourist seasons.
What cultural etiquette should travelers from San Diego be aware of when visiting Chicago?
Travelers from San Diego should be mindful of a few cultural etiquette norms when in Chicago. It is common to greet with a friendly yet reserved manner; a polite 'hello' or nod is appreciated. Tipping is an important aspect of local service culture, with a standard tip of 15-20% in most restaurants. Public decorum in busy areas such as public transit should be maintained by keeping noise levels moderate. Additionally, respectful behavior in historic neighborhoods and cultural institutions is expected to ensure a positive intercultural exchange.
What are the top shopping districts in Chicago for travelers from San Diego?
Chicago’s premier shopping districts offer a vibrant experience ideal for visitors from San Diego. The Magnificent Mile, with its range of luxury boutiques and flagship stores, is a must-visit for upscale shopping. In addition, State Street provides a mix of department stores and unique local shops. For a more eclectic vibe, neighborhoods like Wicker Park feature independent boutiques and vintage shops. Each destination offers varied price ranges, ensuring that travelers can find budget-friendly options as well as premium retail experiences.
Is there a specific time of year when Chicago is best visited by travelers from San Diego?
Yes, many travelers from San Diego find that visiting Chicago during the spring (April to June) or fall (September to October) provides the most enjoyable weather and fewer crowds. During these seasons, temperatures range typically from 55°F to 75°F, which is ideal for exploring the city on foot, enjoying outdoor festivals, and visiting architectural landmarks. These periods also offer a balance of cultural events and less seasonal congestion, ensuring that visitors have a pleasant experience without the extremes of winter chill or summer humidity.
What are the health and safety precautions travelers from San Diego should take when visiting Chicago?
Travelers from San Diego visiting Chicago should adopt common urban safety practices. This includes staying aware of surroundings, particularly in crowded tourist areas, and securing personal belongings to avoid petty theft. It is wise to plan routes in advance and use reputable transportation regarding ride-sharing and taxis; costs generally range from $30 to $50. Additionally, familiarize yourself with local emergency contacts and health facilities. Checking the latest local advisories and following general hygiene practices will help ensure a safe and enjoyable stay in the city.
Are there any seasonal events in Chicago that travelers from San Diego should not miss?
Yes, Chicago hosts several seasonal events that visitors from San Diego should consider including in their itinerary. Notable events include the Chicago Air and Water Show during summer, showcasing aerial acrobatics and waterfront festivities, and Lollapalooza, which often occurs in late summer, bringing a rich mix of music and cultural activities. In addition, winter events such as Christkindlmarket offer an immersive holiday experience with artisanal goods and festive treats. These seasonal events add a unique local flavor to the city’s vibrant cultural calendar.
What are the best solo travel activities in Chicago for travelers arriving from San Diego?
Solo travelers arriving from San Diego can explore numerous enriching activities in Chicago. Self-guided walking tours along the Chicago Riverwalk or architectural boat tours provide deep dives into local design and history. Museums such as the Art Institute or interactive exhibits at the Museum of Science and Industry are excellent choices for independent exploration. Additionally, visiting public parks like Millennium Park offers a chance to relax and observe local culture firsthand. These activities allow for flexible planning and cater well to individuals preferring self-paced discovery.
What unique airport amenities can travelers expect at Chicago O Hare Airport?
Travelers can expect a variety of unique airport amenities at Chicago O Hare Airport that enhance the transit experience. Amenities include art installations, a wide range of dining options from quick bites to sit-down restaurants, and comfortable lounges. Wi-Fi access is generally available throughout the terminals and there are designated relaxation areas. Retail outlets offer local merchandise and essentials, while efficient transport connections such as the CTA Blue Line help in seamless transit into the city. These features ensure that passengers experience comfort and convenience during layovers or before onward travel.
What are the customs requirements for travelers flying from San Diego to Chicago O Hare Airport?
For travelers flying domestically from San Diego to Chicago O Hare Airport, customs requirements are minimal. There is no international customs screening since both cities are within the United States. Passengers will need to present a valid government-issued photo ID such as a driver’s license or passport and undergo standard security screening procedures administered by the TSA. It is advisable to arrive at least 2 hours before departure to accommodate check-in and security processes, ensuring a smooth transition from the departure airport to the terminal.