Don’t laugh, but I haven’t bought airline tickets in more than a decade, and I’m completely ignorant about how to search and find a cheap RT flight nowadays. I’m looking for flights between Oakland, California, and Midway Airport in Chicago anytime in Sept with a stay of, say, three or more days. Where do I even start? How is it done now?
You can play with this https://matrix.itasoftware.com/ and then book direct through airline.
And southwest flies to both your airports https://www.southwest.com/
Looks like your only non-stop flights between OAK and MDW are on Southwest.
Other non-stop flights may require using other nearby airports (e.g. SFO or SJC instead of OAK, or ORD instead of MDW).
Check southwest.com, using the low fare calendar. You can easily find the dates on which the lowest fares are available.
That’s very helpful! I think we might be locked into the Oakland/Midway situation, but I’ll run SFO/ORD too. Perhaps there might be a price difference that would justify the logistical drama that alternative might create.
Would it be safe to assume that Southwest would be the economy choice?
Should I also explore routes that require stop-overs and are not non-stop? Might there be discounting that could make a stop-over fight worth it?
In the old days, I recall making sure to book a ticket that included a Satuday stay over for a cheaper price (leave Friday and return Monday, for example). Is that still even a thing? Are there new rules of thumb?
Southwest won’t necessarily be the cheapest. I just checked Oakland-O’Hare round trips on Orbitz, and Spirit Airlines has cheaper fares. However, on Southwest, checked bags (two per passenger) fly for free, so that can make a big difference in some situations.
It’s my sense that the staying over Saturday is no longer relevant, but I’m not sure.
Southwest allows you to cancel any reservation up to 10 minutes before the flight is scheduled to depart; if the fare is “Wanna Get Away” you don’t get your money back but can use it on another flight within one year. In the other fare categories, I think the fares are fully refundable. I typically book non-Southwest flights using Orbitz, which allows you to cancel with a full refund for approximately 24 hours after making the reservation.
By the way, I rarely fly, but I’m quite conversant with making travel arrangements as the resident travel agent for my two daughters. My crowning glory was figuring out a way to get one daughter back to southern California from central Arkansas on approximately one day’s notice.
For stop-overs, it will probably add two hours to the travel time per stop-over. But they also have increased risk of missed connections (leaving stuck at an intermediate airport until many hours later or the next day when the next available flight is) and mishandling of checked baggage. Generally, adding stop-overs is not worth it unless the price difference is very large or the non-stop or fewer-stop flights do not fit your schedule. In any case, there are very few options even with stop-overs besides Southwest specifically between OAK and MDW.
For SFO to ORD, there are non-stops on United, American, Frontier, and Virgin. For OAK to ORD, there are non-stops on Spirit.
You can use sites like http://www.kayak.com to search many airlines (though not Southwest).
If OAK to MDW non-stop is not the cheapest, then you have to decide for yourself whether the cheaper price of other options is worth the extra hassle of using other airports or extra stop-overs.
Note that if you have checked baggage, be sure to check airlines’ baggage fees before deciding which flight is the least expensive. Spirit also charges for carry-on baggage larger than “personal item” size.
You’ll have more cost options if u broaden your departure & destination airports. Also look at SFO, SJC & ORD.
Try using Expedia.com to shop for fares, but then buy the ticket directly from the airline’s own website. Southwest fares must be purchased directly from its website. SW is not always the cheapest.
Fridays, Sundays, & travel at the start ; end of holiday periods tend to be the highest demand periods for domestic travel, and therefore will have the highest fares. Nonstops tend to be more expensive than connecting flights, but not always.
For someone not experienced in flying, I wouldn’t recommend Spirit. You have to pay for everything - carry ons, changres, food, drinks, checked luggage. If the flight is cancelled, you are S-T-U-C-K. No other airlines will take their tickets.
Check Southwest on Tues. Usually their cheapest fairs are available on Tues. But you must book 14 days in advance if you want a cheap fair. Sometimes 7, but to be safe, 14.
So helpful! Big thanks!
You would,have to pay ME to fly Spirit airlines. Too many added fees.
Are you just trying to get to Chicago area as cheaply as possible or is your visit more focused on say South side of Chicago (eg U Chicago)? If South side, it’s certainly not impossible to get to South side from ORD and back, it’s just more travel time/hassle/some cost both ways that should be figured in deciding ORD v MDW.
Also fly direct if possible. Don’t turn a 4 hour ish flight into a wasted day, especially as flying to Chicago from West Coast there’s a two hour time difference and one or more layovers will make for a very long, wasted day.
In airline jargon “direct” does not mean non-stop. Use “non-stop” when that is what you mean when talking to airlines or travel agents.
^the above is correct.
If there are seats on a nonstop Southwest flight that are not overly expensive, I would buy that over anything else. Stopovers are such a crapshoot. My son was just flying with a 4-5 hour scheduled layover that turned into 9 hours!! Stuck on the tarmac in Newark. Bleh.
I would book non stop Soluthwest flights from Oak to Midway over any other carrier.
And if you dont mind the extra cost, buy business select- that gets you to the front of the line and gives you teh best selection of seats.
The ones midway back on the exit rows have extra legroom- nice to have when on a 4 hr non stop flight.
EarlyBird on Southwest is cheaper than business select, I think, and gets you into Group A boarding. If you check in close to 24 hours before and have EarlyBird, you will likely be at the beginning of the A group.
ear,y bird on SW is only 12.50 each way. We do that.
There was a news headline as I was getting up today about $150 round trip fares from NY to LA, I think. (Sorry, I was pretty groggy at the time.) I would imagine there are comparable savings to other places.
Today might be a very good day to look into this!!!
Thanks! Does one “check in” online up to 24 hours before the flight takeoff time? Are tickets even made of paper anymore? 