What are the most exciting events happening in Chicago, IL?

The best events to attend in Chicago, IL include: Chicago Air and Water Show, an exhilarating display of military and civilian aircraft performing daring maneuvers over Lake Michigan Lollapalooza, a massive music festival featuring top artists across multiple genres in Grant Park Chicago Gourmet, a premier culinary event celebrating the city's vibrant food scene with tastings, cooking demonstrations, and wine pairings.

What are the best holidays to spend in Chicago, IL?

The best holidays to experience in Chicago, IL include: Memorial Day, the unofficial start of summer with vibrant outdoor activities and events Independence Day, spectacular fireworks and festive celebrations throughout the city Labor Day, a lively atmosphere with various festivals and pleasant weather.

Your bookings

San Jose, CA to Chicago, IL Flights

1,000+ travel companies

Scan to get our free app

Use our app to get live travel updates and book mobile tickets for trains, buses, flights, and ferries.

App Store

4.9

42K ratings

Google Play

4.6

136K reviews

Journey information

Overview: San Jose, CA to Chicago, IL flight

USA

Flights from San Jose, CA to Chicago, IL depart on average 30 times per day, taking around 12h 58m. Cheap flight tickets for this journey start at $101 (€85) if you book in advance.

Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.

Price information

Distance

1836 miles (2956 km)

Average flight duration

12h 58m

Cheapest ticket price

$101 (€85)

Flights per day

Direct flights

Airlines

Fastest flight

10h 29m

Cheapest month to travel

October

First flight

17:41

Last flight

20:58

Price information

The cheapest and fastest flights from San Jose, CA to Chicago, IL

Showing times and prices for May 16

Cheapest price

$101

Average price

$354

Fastest journey

10 h 8 m

Average duration

10 h 19 m

Flights per day

Distance

2957 km

Cheap tickets

The best way to find a cheap flight ticket from San Jose, CA to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.

The average ticket from San Jose, CA to Chicago, IL will cost around $354 if you buy it on the day, but the cheapest tickets can be found for only $101.

Fast flights

Of the 2 flights that leave San Jose, CA for Chicago, IL onFri, May 16, 2 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.

On Fri, May 16 the direct flights cover the 2957 km distance in an average of 10 h 19 m but if you time it right, some flights will get you there in just 10 h 8 m .

On Fri, May 16 the longest flights will take 10 h 29 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.

08:58PM10h29

San Jose, CA

07:27AMChicago, IL

$1011One-way

0 transfers

07:35PM10h08

San Jose, CA

05:43AMChicago, IL

$6081One-way

0 transfers

Travel Information

Compare train, bus, and flight for San Jose, CA to Chicago, IL

Omio recommends booking the train as it is the most popular option from San Jose, CA to Chicago, IL among Omio's users. If you are prioritising price take the train with prices starting from €112. For those with little time consider booking a flight which can get you there in 12h 58m. In case you are seeking to minimise your carbon footprint the train is your best bet as it emits only 0.9 - 2.7kg.

Compare flight with

Flight	Most popular Train	Bus
€272 Average price	€261 Average price Cheapest	€321 Average price
15h 58m Average duration Fastest 12h 58m Onboard + 3h 0m Additional time*	2d 63h 47m Average duration 2d 63h 17m Onboard + 30m Additional time*	2d 64h 20m Average duration 2d 63h 50m Onboard + 30m Additional time*
8.9 - 17.7kg CO2 emissions	0.9 - 2.7kg CO2 emissions Lowest	3.0 - 7.4kg CO2 emissions
Direct Options	Direct Options	Direct Options

Additional time: Average total travel duration to departure point, security checks and transfers.

Compare prices and tickets San Jose, CA to Chicago, IL by train, bus, or flight

Fri
May 16

Sat
May 17

Sun
May 18

Mon
May 19

Tue
May 20

Wed
May 21

Thu
May 22

Airlines: United and American Airlines flights from San Jose, CA to Chicago, IL

Travel to Chicago, IL from San Jose, CA from $570 (€478) with Omio’s flight partners United and American Airlines! You can find the best schedules and tickets when comparing and booking the most popular trip for you.

United Airlines is one of the USA’s leading airline and operates domestic and international routes. Economy, Premium Economy and Business are the ticket fares that the airline offers for your next flight between San Jose, CA and Chicago, IL.

Flight information from San Jose, CA to Chicago, IL with United:

Average Duration: 4 h 19 min
Cheapest Price: $570

FAQs: San Jose, CA to Chicago, IL Flight

FAQs: Take a flight from San Jose, CA to Chicago, IL hassle-free. Whether you want fast, cheap or something entirely different, our travel experts have collected everything you need to know so you can find the best option from San Jose, CA to Chicago, IL.

Cheap plane tickets from San Jose, CA to Chicago, IL can start from as little as $64 (€53) when you book in advance. The average flight ticket price for San Jose, CA to Chicago, IL is $216 (€181); however, prices vary depending on the time of day and class and they tend to be more expensive on the day.

On average the San Jose, CA to Chicago, IL flight travel time is 6 h 25 min for the 1833 mile (2956 km) long journey, but the duration can vary if you travel on weekends and holidays.

The earliest flight from San Jose, CA to Chicago, IL leaves at 5: 00AM. Plan your trip with the Journey Planner from Omio.

The latest flight from San Jose, CA to Chicago, IL leaves at 11: 58PM.

There are 30 flights a day from San Jose, CA to Chicago, IL which require at least one change with United. Schedules can vary on holidays or weekends with fewer flights.

When taking a flight from San Jose, CA to Chicago, IL, you can count on United for the best way to get you to Chicago, IL. You can also check all possible airlines who offer a service to Chicago, IL from San Jose, CA and compare the amenities they offer before buying a plane ticket.

The cheapest month for a flight from San Jose, CA to Chicago, IL is November.

It's helpful to compare your options as there are 3 ways to travel from San Jose, CA to Chicago, IL including taking a train, flight or bus.

Since neither San Jose, CA nor Chicago, IL are in the Schengen Area, passport requirements depend on the specific immigration rules of USA and USA. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.

There is a time difference of 2 h between San Jose, CA and Chicago, IL all year round.

The best events to attend in Chicago, IL include:

Chicago Air and Water Show, an exhilarating display of military and civilian aircraft performing daring maneuvers over Lake Michigan
Lollapalooza, a massive music festival featuring top artists across multiple genres in Grant Park
Chicago Gourmet, a premier culinary event celebrating the city's vibrant food scene with tastings, cooking demonstrations, and wine pairings.

The best holidays to experience in Chicago, IL include:

Memorial Day, the unofficial start of summer with vibrant outdoor activities and events
Independence Day, spectacular fireworks and festive celebrations throughout the city
Labor Day, a lively atmosphere with various festivals and pleasant weather.

The best seasons to visit Chicago, IL are Spring or Summer. The best weather to explore Chicago, IL is during May-September.

For domestic flights we recommend to arrive 1.5 to 2 hours before departure. Please check the website of your departure airport if in doubt. Some airports may offer booking time slots for security checks or offer additional information on when to get there based on time of day.

Most airlines permit carry-on bags that fit within specific dimensions (e. G. 22 x 14 x 9 inches or 56 x 36 x 23 cm), including handles and wheels. Bags must fit in the overhead bin or under the seat in front of you.

Many airlines impose weight limits, commonly ranging between 7 kg (15 lbs) and 12 kg (26 lbs).
Typically, passengers are allowed one carry-on bag and one personal item (for example a purse, laptop bag, or backpack). Personal items must fit under the seat in front of you.
Budget Airlines (like Ryanair or Wizz Air) have stricter size and weight limits, often requiring fees for larger carry-ons. Full-Service Airlines have more lenient policies, sometimes including more spacious dimensions or higher weight limits depending on your ticket class.

The list of items prohibited on an airplane varies by country and airline, but in general, the following items are not allowed in carry-on or checked baggage: Weapons and self-defence items, sharp objects, flammable materials, explosives, toxic substances, or liquids over 100ml (except for medications and baby essentials). In checked baggage, firearms (without authorization), explosives, large lithium batteries, and hazardous chemicals are prohibited. Electronic cigarettes must be in carry-on bags, while alcohol and dry ice have restrictions. Always check with your airline for specific regulations.