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Flight INFO & United Airlines(UA) flights from San Jose to Chicago

Cheapest nonstop flight price$49
Cheapest round-trip ticket price$273
Off-season for travelDecember
Peak season for travelApril
Flight distance2,958.96 km
Average flight time5 hours 18 minutes
Popular airlineAmerican Airlines
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Book United Airlines(UA) flights from San Jose to Chicago

  • One way
  • Round-trip
      • direct cheapest
        SJC06:30
        4h 20m
        Nonstop
        ORD12:50
        San Jose - Chicago|Tue, Jan 21|United Airlines
        US$198US$350
        44% OFF
        44% OFF
        US$350US$198

      • SJC06:20
        4h 15m
        Nonstop
        ORD12:35
        San Jose - Chicago|Tue, Mar 4|United Airlines
        US$200US$350
        43% OFF
        43% OFF
        US$350US$200

      • SJC06:30
        4h 20m
        Nonstop
        ORD12:50
        San Jose - Chicago|Mon, Jan 27|United Airlines
        US$204US$350
        42% OFF
        42% OFF
        US$350US$204

      • SJC06:20
        4h 15m
        Nonstop
        ORD12:35
        San Jose - Chicago|Thu, Feb 27|United Airlines
        US$213
        US$213

      • SJC06:30
        4h 20m
        Nonstop
        ORD12:50
        San Jose - Chicago|Wed, Feb 12|United Airlines
        US$215
        US$215

      • SJC06:30
        4h 20m
        Nonstop
        ORD12:50
        San Jose - Chicago|Mon, Jan 13|United Airlines
        US$225
        US$225

      • SJC06:30
        4h 20m
        Nonstop
        ORD12:50
        San Jose - Chicago|Tue, Jan 28|United Airlines
        US$231
        US$231

      • SJC06:30
        4h 20m
        Nonstop
        ORD12:50
        San Jose - Chicago|Tue, Jan 14|United Airlines
        US$232
        US$232

      • SJC06:30
        4h 20m
        Nonstop
        ORD12:50
        San Jose - Chicago|Tue, Feb 4|United Airlines
        US$235
        US$235

      • SJC06:20
        4h 15m
        Nonstop
        ORD12:35
        San Jose - Chicago|Wed, Mar 5|United Airlines
        US$235
        US$235

      • SJC06:20
        4h 15m
        Nonstop
        ORD12:35
        San Jose - Chicago|Mon, Feb 24|United Airlines
        US$235
        US$235

      • SJC06:30
        4h 20m
        Nonstop
        ORD12:50
        San Jose - Chicago|Wed, Jan 22|United Airlines
        US$238
        US$238

      • SJC06:30
        4h 20m
        Nonstop
        ORD12:50
        San Jose - Chicago|Tue, Feb 11|United Airlines
        US$276
        US$276

      • SJC08:25
        13h 48m
        1 stop
        MDW00:13
        San Jose - Chicago|Tue, Jan 14|United Airlines
        US$136
        US$136

      • SJC08:30
        13h 47m
        1 stop
        MDW00:17
        San Jose - Chicago|Tue, Mar 4|United Airlines
        US$146
        US$146

      • SJC12:55
        9h 22m
        1 stop
        MDW00:17
        San Jose - Chicago|Tue, Jan 28|United Airlines
        US$153
        US$153

      • SJC08:25
        13h 48m
        1 stop
        MDW00:13
        San Jose - Chicago|Wed, Jan 15|United Airlines
        US$155
        US$155

      • SJC08:25
        13h 52m
        1 stop
        MDW00:17
        San Jose - Chicago|Wed, Jan 29|United Airlines
        US$155
        US$155

      • SJC12:55
        9h 22m
        1 stop
        MDW00:17
        San Jose - Chicago|Tue, Feb 4|United Airlines
        US$156
        US$156

      • SJC18:55
        27h 22m
        1 stop
        MDW00:17
        San Jose - Chicago|Mon, Feb 17|United Airlines
        US$169
        US$169

      • SJC18:55
        16h 30m
        1 stop
        ORD13:25
        San Jose - Chicago|Mon, Feb 17|United Airlines
        US$170
        US$170

      • SJC08:30
        13h 47m
        1 stop
        MDW00:17
        San Jose - Chicago|Sat, Mar 1|United Airlines
        US$173
        US$173

      • SJC08:25
        13h 52m
        1 stop
        MDW00:17
        San Jose - Chicago|Sun, Feb 9|United Airlines
        US$179
        US$179

      • SJC08:25
        14h 7m
        1 stop
        ORD00:32
        San Jose - Chicago|Sun, Feb 2|United Airlines
        US$180
        US$180

      • SJC08:25
        13h 52m
        1 stop
        MDW00:17
        San Jose - Chicago|Sun, Feb 2|United Airlines
        US$193
        US$193

      • SJC08:25
        13h 34m
        1 stop
        ORD23:59
        San Jose - Chicago|Sat, Jan 18|United Airlines
        US$207
        US$207

      • SJC12:55
        9h 22m
        1 stop
        MDW00:17
        San Jose - Chicago|Tue, Jan 21|United Airlines
        US$208
        US$208

      • SJC08:30
        13h 47m
        1 stop
        MDW00:17
        San Jose - Chicago|Thu, Feb 27|United Airlines
        US$212
        US$212

      • SJC08:30
        6h 26m
        1 stop
        ORD16:56
        San Jose - Chicago|Wed, Mar 19|United Airlines
        US$212
        US$212

      • SJC08:25
        11h
        1 stop
        ORD21:25
        San Jose - Chicago|Wed, Jan 29|United Airlines
        US$213
        US$213

      • SJC01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        San Jose - Chicago|Mon, Jan 20|United Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

📱 eSIM, SIM & WiFi Deals
Grab cheap eSIMs, SIMs, and portable WiFi. Stay connected anywhere!
🔥 Travel Discounts Worldwide
Find latest hot deals on flights, hotels, attractions, and more across different regions!
🚆 Hot Transportation Deals
Get up to 10% OFF Coupon on train tickets in many countries!
Save 10% on car rentals
Check out weekly flight deals & save big!
🎡 Attractions & Discounted Tickets
Enjoy deals on tickets to popular attractions around the globe. Explore more for less! 🎟️

United Airlines(UA) flights from San Jose to Chicago & Flight Schedule

Flight info.
Departure
Arrival
Weekly Schedule

  1. UA1239

    United Airlines

    06:30

    SJC

    4.3h

    Nonstop

    12:50

    ORD

    SMTWTFS
    Search

  2. UA1999

    United Airlines

    08:25

    SJC

    2.6h

    12:04

    DEN

    SMTWTFS
    Search

  3. F93174

    Frontier Airlines

    09:48

    DEN

    2.5h

    13:20

    ORD

    ------S

  4. UA1999

    United Airlines

    08:25

    SJC

    2.6h

    12:04

    DEN

    SMTWTFS
    Search

  5. F92210

    Frontier Airlines

    20:55

    DEN

    2.4h

    00:21

    MDW

    SMTWTFS

  6. UA1999

    United Airlines

    08:25

    SJC

    2.6h

    12:04

    DEN

    SMTWTFS
    Search

  7. UA377

    United Airlines

    20:20

    DEN

    2.5h

    23:52

    ORD

    SMTWTFS

  8. UA1999

    United Airlines

    08:25

    SJC

    2.6h

    12:04

    DEN

    SMTWTFS
    Search

  9. UA1898

    United Airlines

    17:48

    DEN

    2.5h

    21:20

    ORD

    SMTWTFS

  10. UA1999

    United Airlines

    08:25

    SJC

    2.6h

    12:04

    DEN

    SMTWTFS
    Search

  11. UA617

    United Airlines

    13:30

    DEN

    2.6h

    17:05

    ORD

    SMTWTFS

  12. UA1356

    United Airlines

    12:55

    SJC

    2.6h

    16:33

    DEN

    SMTWTFS
    Search

  13. F92210

    Frontier Airlines

    20:55

    DEN

    2.4h

    00:21

    MDW

    SMTWTFS
Show Less

United Airlines(UA) flights from San Jose to Chicago Flight Booking FAQ

  • When are flight tickets from San Jose (SJC) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from San Jose to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from San Jose (SJC) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around $314.

  • How long does it take to fly from San Jose (SJC) to Chicago (CHI) and what is the distance?

    It takes around 5 hours 18 minutes to fly from San Jose (SJC) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

  • What are the most popular airlines that fly from San Jose (SJC) to Chicago (CHI)?

    Airlines with flights from San Jose (SJC) to Chicago (CHI): Southwest Airlines and United Airlines.

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