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serra | Staff 12.1K Views
Sep 2, 2025 4:10 PM

Roundtrip Airfares: Chicago, IL to/from San Diego, CA via Major Airlines BE

$157

$208

24% off
(Travel Oct-Dec 2025)at Expedia
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Deal Details
Various Major Airlines (listed below) is offering Roundtrip Airfare Flight: Chicago, IL (ORD) to/from San Diego, CA (SAN) on sale for $157/traveler via United, American or Alaska Airlines. Travel availability between select dates from October to December 2025 listed below.

Thanks to Deal Hunter serra for finding this deal

Note, select travel departure dates/pricing may vary.

Some flights may be slightly more/less depending on the available timeslot

Available Major AirlinesTravel Availability
  • Departs Chicago, IL, (ORD - O'Hare Intl.)
    • October 2025
      • 4, 7-8, 11, 14-15, 18, 21-22, 25, 28-29
    • November 2025
      • 1, 4-5, 8, 11-12, 15, 18-19
    • December 2025
      • 3, 6, 9-10, 13, 16-17
  • Departs San Diego, CA (SAN - San Diego Intl.)
    • October 2025
      • 4, 7-8, 11, 14-15, 18, 21-22, 25, 28-29
    • November 2025
      • 1, 4-5, 8, 11-12, 15, 18-19
    • December 2025
      • 2-3, 6, 9-10, 13, 16-17

Editor's Notes

Written by Discombobulated | Staff
  • About the Deal
    • Basic economy cabin (nonstop flight): On Alaska, Southwest and American you may have a personal item and a carry-on bag. On United, you may only have a personal item. There is no seat selection and no change.
    • Non-refundable flight and changes are not allowed; additional cost for 1st checked bag
    • Prices may change based on availability and are not final until you complete your purchase
    • Offer valid while pricing/availability last

Original Post

Written by serra | Staff
Community Notes
About the Poster
Deal Details
Community Notes
About the Poster
Various Major Airlines (listed below) is offering Roundtrip Airfare Flight: Chicago, IL (ORD) to/from San Diego, CA (SAN) on sale for $157/traveler via United, American or Alaska Airlines. Travel availability between select dates from October to December 2025 listed below.

Thanks to Deal Hunter serra for finding this deal

Note, select travel departure dates/pricing may vary.

Some flights may be slightly more/less depending on the available timeslot

Available Major AirlinesTravel Availability
  • Departs Chicago, IL, (ORD - O'Hare Intl.)
    • October 2025
      • 4, 7-8, 11, 14-15, 18, 21-22, 25, 28-29
    • November 2025
      • 1, 4-5, 8, 11-12, 15, 18-19
    • December 2025
      • 3, 6, 9-10, 13, 16-17
  • Departs San Diego, CA (SAN - San Diego Intl.)
    • October 2025
      • 4, 7-8, 11, 14-15, 18, 21-22, 25, 28-29
    • November 2025
      • 1, 4-5, 8, 11-12, 15, 18-19
    • December 2025
      • 2-3, 6, 9-10, 13, 16-17

Editor's Notes

Written by Discombobulated | Staff
  • About the Deal
    • Basic economy cabin (nonstop flight): On Alaska, Southwest and American you may have a personal item and a carry-on bag. On United, you may only have a personal item. There is no seat selection and no change.
    • Non-refundable flight and changes are not allowed; additional cost for 1st checked bag
    • Prices may change based on availability and are not final until you complete your purchase
    • Offer valid while pricing/availability last

Original Post

Written by serra | Staff

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10 Comments

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Sep 4, 2025 3:21 PM
359 Comments
Joined Sep 2013
ilovebeermoneySep 4, 2025 3:21 PM
359 Comments
Always wanted to go to Chicago but heard the city is very dangerous. I'm sure there are safe areas though. Anyone want to chime in?
1
1
Sep 4, 2025 3:30 PM
345 Comments
Joined Feb 2010
gramesmithSep 4, 2025 3:30 PM
345 Comments
Quote from ilovebeermoney View quoted comment :
Always wanted to go to Chicago but heard the city is very dangerous. I'm sure there are safe areas though. Anyone want to chime in?
it could be cold within these travel dates and hence the offer, depends on your luck. You could get some nice fall views though if you come in October.

About the safety part unless you are going to the south side you will be fine, some nut cases were shooting bullets at cars on the highway a few years ago
Sep 4, 2025 4:04 PM
709 Comments
Joined Sep 2009
coffeerequiredSep 4, 2025 4:04 PM
709 Comments
Quote from ilovebeermoney View quoted comment :
Always wanted to go to Chicago but heard the city is very dangerous. I'm sure there are safe areas though. Anyone want to chime in?
you get a free mugging with your coffee
its a slickdeal!
1
Sep 4, 2025 5:21 PM
20 Comments
Joined Nov 2007
ArvSep 4, 2025 5:21 PM
20 Comments
Quote from ilovebeermoney View quoted comment :
Always wanted to go to Chicago but heard the city is very dangerous. I'm sure there are safe areas though. Anyone want to chime in?
Not really. Looking at Wikipedia's 2024 crime rates by city (per 100,000 people), it has 1/4 the violent crime rate of Oakland, 1/3 of Baltimore, and 2/3 of Los Angeles. About 20% higher than San Diego. Avoid the South Side of Chicago (where a majority of the crime happens) and it is for the most part a clean, safe city.

October should still be a good time (think 60-70 degress on average), but later might be a bit chilly.
Sep 4, 2025 6:22 PM
5.6K Comments
Joined Mar 2007
LeonidasSep 4, 2025 6:22 PM
5.6K Comments
Quote from ilovebeermoney View quoted comment :
Always wanted to go to Chicago but heard the city is very dangerous. I'm sure there are safe areas though. Anyone want to chime in?
Living in Chicago for over a decade. The main touristy areas are all very safe. A lot of history, arts, culture, and food here. Come in early Oct and read the book "Devil in the White City" before coming.
Sep 4, 2025 6:26 PM
4.9K Comments
Joined Jan 2007
geoffkinSep 4, 2025 6:26 PM
4.9K Comments
This is mainly for Chicago to visit San Diego BEACHES!
Sep 4, 2025 7:39 PM
2.8K Comments
Joined May 2015
justyeSep 4, 2025 7:39 PM
2.8K Comments
Quote from ilovebeermoney View quoted comment :
Always wanted to go to Chicago but heard the city is very dangerous. I'm sure there are safe areas though. Anyone want to chime in?
Every major American city has a ghetto area that no reasonable person of means spends any time in. The violence and crime is mostly isolated to those areas and the victims are typically residents of those low income, crime infested zones, not tourists or middle class or wealthier folks. Chicago isn't Oakland or St. Louis.

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Sep 5, 2025 4:42 AM
157 Comments
Joined Jun 2025
JustHere4TheZiplineSep 5, 2025 4:42 AM
157 Comments
Quote from ilovebeermoney View quoted comment :
Always wanted to go to Chicago but heard the city is very dangerous. I'm sure there are safe areas though. Anyone want to chime in?
The main downtown area is super safe from am to pm. Most of the violence is in areas you wouldn't ever go to.
Sep 6, 2025 6:39 AM
284 Comments
Joined Jan 2015
HiroxSep 6, 2025 6:39 AM
284 Comments
Quote from JustHere4TheZipline View quoted comment :
The main downtown area is super safe from am to pm. Most of the violence is in areas you wouldn't ever go to.
Agreed. I lived there for many years. It's not subtle where you shouldn't be walking.If Trump sends the National Guard there, I'm so curious where they will be deployed: the high crime areas or the high political areas.
Original Poster
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Deal Hunter
Sep 8, 2025 2:11 PM
93.5K Comments
Joined Jul 2004
serraSep 8, 2025 2:11 PM
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