Here's a fantastic deal matching what Spirit Airlines usually offers on this route pairing. With a price this nice, there's sure to be a few strings attached. Firstly, it's only available on select scattered dates through early November and then again in January into early February. So those in Chicago might want to fly to LA for that winter period, and all the LA-based flyers might want to search for the fall version of these fares to Chicago.
A tactic you can use for better availability is to book two separate one-way trips if you can't find your exact dates on one airline. Pair a United and American one-way fare to stitch together an itinerary that better suits your travel needs.
After you've found the dates that work best, take note that the United fares in Basic Economy still only allow a small personal sized item that can fit under the seat in front of you. American is a little more generous and allows a standard sized carry-on that you can put in the overhead locker, so with all prices being equal lean toward AA's fares if you need the extra packing room.
As an example below, I was able to find seats departing LAX on Thursday, January 24 and returning from ORD on Monday, January 28, 2019.
If you haven't spent some time today dreaming up other amazing destinations you could fly to for less. Why not head on over to our Los Angeles (LAX) and Chicago (ORD) flight deal pages for some travel inspiration.
Need a hotel in the Windy City for the sample travel dates? Hotelwatchdog has you covered with a full list of available rooms here.