Chicago is an amazing city for a first visit, and it sounds like you're already planning a fun trip! Since you like food and charming neighborhoods, make sure to explore Lincoln Park, Andersonville, and Old Town—these areas are full of character and great for walking. Don’t miss out on the Chicago Riverwalk and Millennium Park for iconic sights and relaxing strolls.

For rooftop drinks, consider Cindy’s Rooftop for a fantastic view of Millennium Park or the J. Parker, which overlooks Lincoln Park. Both spots are perfect for a night out!

As for activities, while exploring big cities like Chicago is exciting, if you ever find yourself in Florida, a boat rental in Naples is a wonderful way to unwind. It’s the perfect contrast to city life—peaceful waters, beautiful sunsets, and a chance to relax after exploring charming neighborhoods on foot.

Enjoy Chicago and let us know how it goes! https://www.gatorboatrentals.com/naples-boat-rental

Chicago bro here. some good recs above. a few things to add:

-Try to score a meal at the Walnut Room at Macy's during the holidays
-if you go to Christkindl market downtown, grab a beer at the Berghoff nearby
Restaurants:
-Bavettes (eat at the bar)
-La Scarola
-Aba (west loop)
-Pizza'mici just opened and may be the best tavern style in the city (may still also be BYOB)


And some more cozy options:

https://www.timeout.com/chicago/restaurants/chicago-restaurants-and-bars-with-fireplaces

No to Wiener’s Circle. They will have to stand outside and eat a hot dog in December. Unless you’re super drunk at 12am that’s a no.

And no to rooftop drinks. That’s a summer thing only.

Plan on indoor things. Museums, shows, dining unless you get a mild night then the Christkindlemarket or viewing lights.

Anonymous wrote:No to Weiner Circle.

Ming Hin for delicious Chinese
Cindy’s Rooftop
London House rooftop
Curling & cocktails at the Gwen
Mr. Beef (inspiration for tv series The Bear)
Starbucks Roastery
Christkindlemarket

Bundle in layers. Chicago is beautiful at Christmas. Have fun!

OP: If you like hot dogs, don't miss Weiner's Circle

Pp here, also:

Butch McGuire’s for over the top Christmas decorations
The Gage
The Girl and the Goat (West Loop, so an Uber away)

No to Weiner Circle.

Ming Hin for delicious Chinese
Cindy’s Rooftop
London House rooftop
Curling & cocktails at the Gwen
Mr. Beef (inspiration for tv series The Bear)
Starbucks Roastery
Christkindlemarket

Bundle in layers. Chicago is beautiful at Christmas. Have fun!

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:How long is the winter?
High tea and a spa sound great.

I've done tea at the Drake. It's lovely. And convenient for OP. If I wanted to splurge, I'd try the Peninsula. Bet their spa is pretty solid, too.

Also, hotels will be decked out for the holidays. High tea should feel particularly festive.

It's afternoon tea. Not high tea. Sorry to get pedantic, but it's a pet peeve. Afternoon tea is the fancy thing in the afternoon with finger sandwiches and scones at a beautiful hotel. High tea is basically an early and very casual dinner in your house.

Got it, thanks for the correction. I would like both, please.

Anonymous wrote:

Anonymous wrote:How long is the winter?
High tea and a spa sound great.

I've done tea at the Drake. It's lovely. And convenient for OP. If I wanted to splurge, I'd try the Peninsula. Bet their spa is pretty solid, too.

Also, hotels will be decked out for the holidays. High tea should feel particularly festive.

It's afternoon tea. Not high tea. Sorry to get pedantic, but it's a pet peeve. Afternoon tea is the fancy thing in the afternoon with finger sandwiches and scones at a beautiful hotel. High tea is basically an early and very casual dinner in your house.

Anonymous wrote:How long is the winter?
High tea and a spa sound great.

I've done tea at the Drake. It's lovely. And convenient for OP. If I wanted to splurge, I'd try the Peninsula. Bet their spa is pretty solid, too.

Also, hotels will be decked out for the holidays. High tea should feel particularly festive.

Anonymous wrote:How long is the winter?
High tea and a spa sound great.

It got cold earlier than usual this year. It's typically cold well into March. But one March I went to LA - it was 85 in Chicago and 50s/rain in LA. I grew up here (lived in D.C. for 7 years and work for a federal agency - hence still on this site), and winters are less harsh with far less snow than when I was younger.

How long is the winter?
High tea and a spa sound great.

So. . . I'm in Chicago now. It's 27 with a windchill of 14. You may get lucky - or not. But it's not the ideal time for charming neighborhood exploration - of which there are many.

I wouldn't typically recommend Streeterville, but given that it's likely going to be cold, it's not a terrible choice. Options for reasonably-priced or smaller, independent restaurants are going to be limited in that neighborhood with its high rents.

The Art Institute is a must. Plan the day there and perhaps see about joining a tour.

If you get decent weather, you could head to Pilsen to visit the Mexican art museum and try a Mexican restaurant or two. Pilsen has a good bit of grit, but it worthy of a stop if you don't have solid Mexican food near you. And Thalia Hall often has good concerts, but you'll want to plan in advance.

I also really like the Museum of Contemporary Art, which should be close to you.

I like PP's suggestion of the Lincoln Park Conservatory. Though I far prefer the Garfield Park Conservatory, LPC is easier to get to and has many food options - including Wiener Circle - nearby. If the weather's nice, you can also hop over to the zoo, which is free and has loads of indoor exhibits. The lion cubs are particularly adorable, though I haven't seen them in winter. From the LPC, hop a quick cab over to Clark and Armitage. From there you can walk west and do a bit of poking your head into shops as you get cold. The streets north and south of there are rather charming, with many old homes.

You could see about doing high tea in a fancy hotel - several options near you most likely. Many of them will also have nice spas. Visit the Christmas market (Christkinlmarket) at Daley Plaza.

See what's going on for live music. Chicago has live blues and jazz seven nights a week. Do a bit of research and you'll surely find many options. As PP mentioned, there's the Green Mill and you can get there in about 30 minutes on the Red Line train. There are some good Asian food options (lots of Vietnamese + Sun Wah for Chinese) and Demera for Ethiopian up there. It's not a particularly charming neighborhood, though. Some of the residential streets are nice, but it's not a place to explore after dark.

And come back in the summer. Things are green and folks are outside and active. Many of us just hunker down with friends and family in the winter.

Thanks so much! December is probably not the best time to fall in love with Chicago

I lived in Chicago for 10 years and miss it terribly. If it weren't for DH, I would have moved back years ago.

I head right for Weiner's Circle on Clark for a char Chicago dog. For me, hot dogs are not right if they don't have celery salt, lol.

I also always eat pizza at Lou Malnati's.

Art Institute is a must. It used to be free on Tuesdays and I would go and stare at the Chagall windows. The Lincoln Park conservatory is such a peaceful place, I used to go all the time. Walk along the lake front.

The Green Mill for music or poetry slam (if they still do poetry slams there?).

And as far as "charming neighborhoods" go, they definitely exist. Lots of them. Favorites that I lived in: Ravenswood near Lincoln Square and Wicker Park (I lived at the border of Ukrainian Village). There is Lincoln Park as well, but it's expensive. Andersonville, especially if you are queer. Lots and lots of cool neighborhoods.

Two girl friends in their 40s. What would you do?
First time in Chicago. We like food, some sites, charming neighborhoods (do they exist.) and walking. Also, recommendations for rooftop drinks.
Staying in Streekerville, no car.
Considering relocating