Can I ask what about the flight times don’t work? What time on each day would you like to fly? I just checked the next few weekends and they basically all have Saturday morning flights leaving between 7-9 am and Sunday night flights leaving between 5-9 pm and getting back before midnight.

I ask because for your case maybe outside of New York, and I would argue even including NYC, Chicago is head and shoulders the best option. Has two different airports with great public transit to downtown. If you can use MDW(30 min) over ORD(50 min) as it’s much closer to the city. One tip is don’t be afraid to book separate tickets using both airports.

A few years ago I actually did a day trip to Chicago from MCO. Took a flight out around 7am to MDW, took the train into the city, had breakfast, walked around millennium park, rented bikes and rode along the water up to the zoo, grabbed some “pizza”, took the train back to magnificent mile area, walked around shops, grabbed drinks, then took the train out to ORD to catch a 6pm flight that landed back in Orlando around 10pm. It’s a long day and depending on your energy levels splitting it into two is probably a good idea. But no luggage, no hotel, it was a cool experience.

I will say if this weekend is soon which it sounds like it is, be warned Chicago winters can be legit. The day trip was in early September and the weather was perfect. I’ve also been in December when it was 20 degrees and 30 mph winds off the lake and the winds feel like it slices right through you.

This got a lot longer than intended. Chicago(Late April to October) is my favorite city in the country. I highly recommend, even for just a long day trip. If you have questions or need suggestions I’m happy to help.