hi. What is the best airfare currently available for roundtrip travel
from San Francisco to Chicago (any airport), May 24-28, 2002? I need to leave
on Friday the 24th after 10:00 p.m. (i.e. i want to take the red-eye)
and then on Tues I want to take a flight back around 8:00 a.m. I can
also leave from San Jose.
I would prefer to have direct flights both ways. 
thank you

Finding the cheapest flight can be difficult. There are a number of
online service providers that list fares depending upon the search
criteria. Orbitz, Expedia, Travelocity and Cheap Tickets to name just
a few. Only Expedia does not require free registration to view fare
info. There are also other methods for finding cheap fares and that
includes viewing individual airlines own websites for weekly discounts
and looking in one's local magazine for printed specials.

Since your flight requirements are fairly specific, using services
such as Orbitz, Expedia, or Travelocity provide the quickest
assessment of how much it will cost and whether such flights are
available. Listed below are flights that meet your needs as closely as
possible from each of these services. Please note that these prices do
change throughout the day as availability for these flight decreases.

The cheapest flight that meets all of your requirements can be
purchased through Orbitz by doing a search for a nonstop flight from
SFO to CHI on May 24th, returning May 28th. It is $226 and is on
United Airlines. The flight departs Friday at 11:45pm from SFO and
returns leaving CHI at 8:10am on Tuesday, May 28th. Note that this is
not to say a cheaper flight does not exist, it just could not be found
at this time.

 
Orbitz.com
http://www.orbitz.com/

Roundtrip SFO
  
$196  airfare  $5  service fee $201  trip cost  
United Airlines 152
Fri, May 24 11:45p-5:34a   San Francisco (SFO)   Chicago (ORD)
total duration: 3h 49min
United Airlines 143
Tue, May 28 11:50a-2:16p   Chicago (ORD)   San Francisco (SFO)
total duration: 4h 26min

$221  airfare  $5  service fee $226  trip cost  
United Airlines 152
Fri, May 24 11:45p-5:34a   San Francisco (SFO)   Chicago (ORD)
total duration: 3h 49min
United Airlines 809
Tue, May 28 8:10a-10:39a   Chicago (ORD)   San Francisco (SFO)
total duration: 4h 29min

Roundtrip SJC
  
$306  airfare  $5  service fee $311  trip cost  
United Airlines 1268
Fri, May 24 11:00p-4:55a   San Jose (SJC)   Chicago (ORD)
total duration: 3h 55min
United Airlines 345
Tue, May 28 3:15p-5:45p   Chicago (ORD)   San Jose (SJC)
total duration: 4h 30min


Expedia.com
http://www.expedia.com/

Departing SFO

from $198  
11:45 PM Depart San Francisco (SFO)
Arrive Chicago (ORD) 5:34 AM +1 day  Fri 24-May
3hr 49mn    United Airlines 152 
Nonstop flight

from $306  
11:20 PM Depart San Francisco (SFO)
Arrive Chicago (MDW) 5:19 AM +1 day  Fri 24-May
3hr 59mn    ATA 136 
Nonstop flight
 
from $308  
11:15 PM Depart San Francisco (SFO)
Arrive Chicago (ORD) 5:04 AM +1 day  Fri 24-May
3hr 49mn    United Airlines 34 
Nonstop flight
 
from $308  
11:50 PM Depart San Francisco (SFO)
Arrive Chicago (ORD) 5:47 AM +1 day  Fri 24-May
3hr 57mn    American Airlines 1608 
Nonstop flight
 
Returning SFO

from $308  
8:10 AM Depart Chicago (ORD)
Arrive San Francisco (SFO) 10:39 AM  Tue 28-May
4hr 29mn    United Airlines 809 
Nonstop flight
 
from $1425  
8:40 AM Depart Chicago (MDW)
Arrive San Francisco (SFO) 11:16 AM  Tue 28-May
4hr 36mn    ATA 273 
Nonstop flight
 
Departing SJC

from $308  
10:55 PM Depart San Jose (SJC)
Arrive Chicago (ORD) 4:53 AM +1 day  Fri 24-May
3hr 58mn    American Airlines 878 
Nonstop flight
 
from $308  
11:00 PM Depart San Jose (SJC)
Arrive Chicago (ORD) 4:55 AM +1 day  Fri 24-May
3hr 55mn    United Airlines 1268 
Nonstop flight
 
from $350  
11:54 AM Depart San Jose (SJC)
Arrive Chicago (ORD) 8:05 PM  Fri 24-May
6hr 11mn    America West 7 
1 stop
 
Returning SJC

from $485  
8:47 AM Depart Chicago (ORD)
Arrive San Jose (SJC) 1:46 PM  Tue 28-May
6hr 59mn    American Airlines 827 / 1376 
Connect in Orange County (SNA)
 
from $619  
8:59 AM Depart Chicago (ORD)
Arrive San Jose (SJC) 11:26 AM  Tue 28-May
4hr 27mn    American Airlines 2007 
Nonstop flight
 
 
Travelocity.com
http://www.travelocity.com/

Roundtrip via SFO

Total:  USD  198.00   
May 24 
11:45pm Depart - San Francisco, CA (SFO)     United Airlines 152 
5:34am Arrive - Chicago-OHare (ORD) Nonstop 
Total travel time:3 hrs 49 min    
May 28 
2:44pm Depart - Chicago-OHare (ORD)     United Airlines 135 
5:15pm Arrive - San Francisco, CA (SFO) Nonstop 
Total travel time: 4 hrs 31 min  

Roundtrip via SJC

Total:  USD  308.00   
May 24 
10:55pm Depart - San Jose, CA (SJC)     American Airlines 878 
4:53am Arrive - Chicago-OHare (ORD) Nonstop 
Total travel time:3 hrs 58 min    
May 28 
12:18pm Depart - Chicago-OHare (ORD)     American Airlines 97 
2:47pm Arrive - San Jose, CA (SJC) Nonstop 
Total travel time: 4 hrs 29 min  

Total:  USD  308.00   
May 24 
11:00pm Depart - San Jose, CA (SJC)     United Airlines 1268 
4:55am Arrive - Chicago-OHare (ORD) Nonstop 
Total travel time:3 hrs 55 min    
May 28 
3:15pm Depart - Chicago-OHare (ORD)     United Airlines 345 
5:45pm Arrive - San Jose, CA (SJC) Nonstop 
Total travel time: 4 hrs 30 min  


Additional information: 
 
Orbitz 
http://www.orbitz.com 
 
Expedia 
http://www.expedia.com/ 
 
Travelocity 
http://www.travelocity.com/ 

Cheap Tickets
http://web.cheaptickets.com/index.html
 
Google Category: Recreation > Travel > Budget > Air 
http://directory.google.com/Top/Recreation/Travel/Budget/Air/ 
 
Google Category: Recreation > Travel > Reservations > Air > Airlines 
http://directory.google.com/Top/Recreation/Travel/Reservations/Air/Airlines/
 
Google Category: Recreation > Travel > Budget > Air > Advice and
Information
http://directory.google.com/Top/Recreation/Travel/Budget/Air/Advice_and_Information/
 
Google Recreation > Travel > Budget > Auctions and Bids 
http://directory.google.com/Top/Recreation/Travel/Budget/Auctions_and_Bids/?tc=1/


Search terms used:

cheap airfare
://www.google.com/search?q=cheap+airfare

cheap travel
://www.google.com/search?q=cheap+travel

This answer was useful and put me on the right path and gave me a
rnage of what top expect. in the end though I purchased a ticket for
slightly cheaper with similar times on American Airlines.

Hotwire(http://www.hotwire.com - need to create an account to search)
is another good site to search for cheap airfare.  The only downside
is that you can not specify times, nor will you know the times of the
flight until you make the purchase.  I've had good luck with it:
No more than a week..probably a few days.. before I needed to make a
trip from Rochester, NY (ROC) to CHI, I checked out Hotwire.  Round
trip ticket only cost me $128 - not too bad for last minute and the
times actually worked out fairly well.

A trip from SFO to CHI from May 24-28 is going for $184.  If you're
flexible with your times, Hotwire is great.

I have had amazing luck with Priceline in the past. One time last year
I had to make an emergency one-day trip from Baton Rouge to San Jose.
It was Saturday, and I needed to fly on Sunday or Monday. I put in my
bid of $100 on Saturday afternoon, and it was accepted within 15
minutes. I flew out Sunday and returned on Tuesday. I shudder to think
what the list price would have been.

Bill

Southwest Airlines now flies nonstop from Chicago Midway to Oakland. 
But, alas, they don't tend to offer red-eyes.  Their fares, along with
JetBlue, another lowfare carrier don't tend to show up in Orbitz,
Travelocity, and the like.