Cheap flights from San Jose to Chicago from £100

Cheap flights from San Jose to Chicago from £100

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1 stop
Wed, Apr 29
San Jose SJCChicago ORD

£100
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Direct
Wed, Apr 29
San Jose SJCChicago ORD

£102
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1 stop
Wed, Apr 29
San Jose SJCChicago ORD

£109
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1 stop
Tue, Apr 28
San Jose SJCChicago ORD

£109
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Direct
Sat, May 2
San Jose SJCChicago ORD

£128
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Direct
Tue, Apr 28
San Jose SJCChicago ORD

£137
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1 stop
Mon, Apr 27 – Sat, May 2
San Jose SJCChicago ORD

£223
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1 stop
Mon, Apr 27 – Sat, May 2
San Jose SJCChicago ORD

£223
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1 stop
Tue, Apr 28 – Fri, May 1
San Jose SJCChicago ORD

£237
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1 stop
Tue, Apr 28 – Fri, May 1
San Jose SJCChicago ORD

£237
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1 stop
Tue, Apr 28 – Fri, May 1
San Jose SJCChicago ORD

£248
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Direct
Tue, Apr 28 – Thu, Apr 30
San Jose SJCChicago ORD

£282
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Getting from Chicago's airport to the city center

Chicago is served by two major airports, each offering a variety of airport transfers to city center destinations. O'Hare International Airport (ORD) lies 27 km northwest of downtown Chicago, while Chicago Midway International Airport (MDW) is located 16 km southwest of the city center. Transport options include the CTA rapid transit trains, buses, taxis, ride-hailing services, and private transfers. Journey times and costs vary depending on the airport, time of day, and traffic conditions.

From O'Hare International Airport (ORD)

From Chicago Midway International Airport (MDW)

Notes:

  • Prices in USD; table created in 2025 and subject to change.
  • CTA Ventra cards or contactless payment accepted on Blue and Orange Lines.
  • Taxis are metered; ride-hailing prices vary with demand. Road traffic can significantly affect journey times.
  • We recommend checking official transport websites for your travel planning.

Updated: December 2025

Key info about flying to Chicago

Depart from
San Jose International
Arrive to
O Hare International
Average flights per week
292
Flight distance
2940 km
Worth visiting
Art Institute of Chicago

Weekly direct flights

Discover the top airlines offering direct flights from San Jose to Chicago in the next month. You’ll find the number of daily direct flights per airline in the chart.

AirlineMon 06.04Tue 07.04Wed 08.04Thu 09.04Fri 10.04Sat 11.04Sun 12.04
1111111
Weekly flights: 7 totalDaily flights: 1 averageMost flights: Monday 1 flights
AirlineMon 13.04Tue 14.04Wed 15.04Thu 16.04Fri 17.04Sat 18.04Sun 19.04
1111111
Weekly flights: 7 totalDaily flights: 1 averageMost flights: Monday 1 flights
AirlineMon 20.04Tue 21.04Wed 22.04Thu 23.04Fri 24.04Sat 25.04Sun 26.04
1111111
Weekly flights: 7 totalDaily flights: 1 averageMost flights: Monday 1 flights
AirlineMon 27.04Tue 28.04Wed 29.04Thu 30.04Fri 01.05Sat 02.05Sun 03.05
1111111
Weekly flights: 7 totalDaily flights: 1 averageMost flights: Monday 1 flights

Check-in for a flight from San Jose to Chicago

NameCarrier codeIATA CodePassport needed during booking
Frontier AirlinesFFTF9No
Hawaiian AirlinesHALHANo
Alaska AirlinesASAASNo
WestJetWJAWSNo
Spirit AirlinesNKSNKNo

Weather in Chicago

Average Weather

MonthAverage monthly max temperatureAverage monthly min temperature
January-1°C-6°C
February0°C-5°C
March6°C0°C
April11°C4°C
May17°C10°C
June22°C16°C
July26°C20°C
August25°C19°C
September22°C16°C
October15°C10°C
November8°C3°C
December2°C-1°C
Hottest Month
26°C
July
Coldest month
-6°C
January
Sunny days
257
days per year
Snow days
17
days per year

14 day forecast

Saturday
11 Apr
85%
10°C4°C
18 Apr
88%
7°C5°C
Sunday
12 Apr
86%
23°C9°C
19 Apr
88%
7°C5°C
Monday
13 Apr
85%
23°C14°C
20 Apr
10°C5°C
Tuesday
14 Apr
78%
20°C17°C
21 Apr
82%
16°C8°C
Wednesday
15 Apr
88%
19°C13°C
22 Apr
84%
21°C10°C
Thursday
16 Apr
83%
20°C12°C
23 Apr
14°C9°C
Friday
17 Apr
74%
24°C12°C
24 Apr
69%
7°C4°C
Book your trip to arrive at O Hare International, Chicago Midway International, or Chicago Rockford International. The distance between San Jose and Chicago is 2940 km. The most popular airlines for this route are Frontier Airlines, Hawaiian Airlines, Alaska Airlines, WestJet, and Spirit Airlines. San Jose and Chicago have 292 direct flights per week.

Frequently asked questions

How long does it take to travel from San Jose to Chicago?
What is the flight distance between San Jose and Chicago?
What airlines offer nonstop (direct) flights between San Jose and Chicago?
What are the most popular routes to and from San Jose?
What are the most popular routes to and from Chicago?
What airports are near San Jose?
What airports are near Chicago?
Which airlines fly between San Jose and Chicago?
When’s the best time to travel between San Jose and Chicago?
What flights operate between San Jose and Chicago?
How many airports are there near San Jose?
How many airports are there near Chicago?
What time do nonstop (direct) flights between San Jose and Chicago depart?
What time do nonstop (direct) flights between San Jose and Chicago arrive?
What time do flights between San Jose and Chicago depart?
What time do flights between San Jose and Chicago arrive?

Explore alternative trips

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Popular routes

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