Is it worth going to Chicago for a single day?

Hi everyone.

If you’ve heard the news, We will no longer have flights to O’Hare on United beginning September 5, 2018, Though we can still go on Southwest, but into Midway.

I would like to go, mainly just to planespot in O’hare for a couple of hours and then fly back.

I honestly want to do this just to fly the last flights before it is discontinued for good, and so I can make a trip report as well.

Would it be worth the $509.00 for the whole trip?


Don’t spend that much money on just a plane spotting trip. If you do decide to go, also visit the city and see the sights. Chicago has a beautiful downtown area and lakefront!


I would arrive into Chicago around 8am, and leave Chicago around 2pm.
So roughly only 5 hours being in Chicago.

Would that be an issue? I would also like to go see Chicago, as they have plenty of transportation so that I don’t have to use a taxi or rent a car

Or I can fly in the day before and leave the next day.

I can’t afford too much atm

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I wouldn’t recommend it but ultimately it’s up to you. If you think it’s worth 500 dollars to plane spot by all means go ahead.

Personally, I think $500 is way to much for Southwest. I can fly round trip from Baltimore to the Caribbean for around $240 on southwest. And just for plane spotting I would not waste your money. Look for cheaper options or wait for a Southwest “get-a-way” deal where the prices drop to around $50 per person. You can always look at other airports like Dallas, Atlanta, Los Angeles as well

This is on United, not Southwest

Oh. I thought you were suggesting for Southwest. Deleting comment now lol

I still personally think 500 dollars is to much. But it is up to you (:

You gave me an idea. I’ll just fly one way on WN to MDW and fly back on UA home


If only I could put in numbers how many times I asked my parents to go to China for a week…

(We didn’t go)

If you want to do it, go for it. That seems like a big deal for your airport so I think it would be fun. Honestly it’s your money so…

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I would recommend taking an early morning flight that gets you to Chicago at around 8-9 like you said, and then take a late flight home, departing around/after 6 PM.

Keep in mind if you do fly into MDW or ORD that both airports are located around the outskirts of the city. It’s at least a 30 minute cab ride and a 50 minute train/subway ride, so that’s another two hours that you lose, traveling from the airport to the downtown and back.


I recommend getting a round-trip flight so you can stay in Chicago for 3-5 days because that is my recommended stay time in Chicago because there is so much to see. You can also planespot during that time.

Just my advice.

Good Day, SouthernDude


That is a idea. I know southwest has to be cheaper that United so if you want to save money I would go with WN. I just comes down to what airport you are flying out of

Fly to MDW, don’t spot there though, not that much interesting. Then take the train to ORD and do some spotting there. You HAVE to visit Tortas Frontera when at ORD.

If that first flight gets delayed your 5 hours are going to dry up real fast. Not what I would do but it’s your trip…

I don’t think it’s worth it at all, especially if you are trying to save money.

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It is not worth it unless you stay at least two nights in the city. The beach near the John Hancock building is a great place to plane spot too as planes come in from the lake. I did that when I used to live there.

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Waste of money in my opinion you could buy more plane spotting equipment for that money

If you are saving money fly out of BOS it is only $225 to go for a few hours

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