US Travel Question: Eve layover in ATL or CHI?

I would choose Chicago, although you will have quite a ride into the city if you are coming into O’Hare.

There are lots of great neighborhoods in Chicago. You can easily find a great restaurant and then go and listen to some blues. It depends on if you want pricey or ethnic. This site has a really good listing. I would recommend a steakhouse as Chicago has excellent beef.

If it’s winter I would choose Atlanta. Bad weather could cause problems in Chicago. I try to avoid any stops in northern cities in the winter whenever I can.

I also would choose Atlanta. The odds of bad weather closing the airport is lower. Coming back from the Carribean you will probably be tired and not want a late night with lots of winter travel to and from the airport.

Can you kick the next day’s flight into the afternoon? That would leave time to do something without rushing the next day.

Chicago can be very romantic in winter and I think it has more to offer than Atlanta. Weather is too unpredictable. It could be sunny and 40F in Chicago and 34F and icy in Atlanta the day you travel. You never know. I would choose the city that has more to offer if that is what you are looking for.

I live in Chicago and love the city because it’s the best place on Earth. So I can offer completely non-biased advice. Come to Chicago!

Coming from the Caribbean on your way to the West Coast, I assume you will not be lugging your snow clothes. And an evening is a super short stay, so you aren’t going to get to know the city.

So I say concentrate on a fabulous room with a nearby restaurant.

Depending on what appeals to you, I would say get a place 40 or more floors high with a spectacular view.

Or a neighborhood B&B or spa.

Meaning something like this or something like my neighborhood B&B

Feel free to PM me with any questions, or post them here for posterity!

Chicago hands down has so much more to offer.
I have travel to both cities often on business over many years and prefer all that Chicago has to offer anytime of the year. I have chosen Chicago as a pleasure visit city many times over to Atlanta of other cities.
Based on your post I am going to throw out considerations about travel issues because they can happen in either place in the winter.
Hotel recomendations:
Hotel Burnham, The Drake, Park Hyatt or Fairmont
Restaraunts:
Bistro Campagne, Cafe Absinthe, Everest, Carlo’s, mk, North Pond, Prosecco, Spiaggia

Plenty of great Blues Clubs too…..

Yes, I’m going to go with Chicago too because I’ve had a couple of great “layovers” there. One time, in college, on a road trip home from Portland, OR, to the east coast, we had to drop a guy off in Chicago and we spent the night and it just happened that Dizzy Gillespie was playing at one of the jazz clubs there and it was just wonderful to get a chance to see him in that sort of venue. Then on a cross country train trip from Oregon to Philly, I had a 5 hour layover in Chicago and I asked and architect friend of mine to set up a little walking tour of some buildings in Chicago, near the train station, and that was great too; but that was during the day and not in winter. Maybe @jaytkay can suggest a little jazz club where you can get some dinner and still get back to your hotel and get a good night’s sleep for your early flight. That’s what I would do; layover in Chicago and go to a nice jazz club.

I choose Chicago too and honestly you don’t have to come into the city from O’Hare to have a grand time. There are some very good hotels like Hotel Intercontinental, excellent restaurants like Gibson’s Steakhouse, bars and activities to keep you busy on a short afternoon with an early flight the next day. A trip into the city from O’Hare can be a nightmare depending on weather and weekend events.