Please sign in to post.
Posted by
6705 posts

I have NOT spent enough time in Chicago — just one October weekend. I would love to be able to spend some more time there and get to know it better.

Posted by
6753 posts

WE loved every minute we lived there. COVID has changed it, hopefully only temporarily.

Posted by
1770 posts

I’m very glad to see Chicago receive this recognition. We have visited many times over the years and always had a great time. I think it has been underrated big time for a long time.

Posted by
6065 posts

I've been to Chicago many times over the years, both on business and family business. I think the best parts of it are the ethnic enclaves and neighborhoods with character, food and history - Bucktown, Greek Town, and Lincoln Square for example.

Plus they do have a nice Christmas Market, for those craving that.

Posted by
888 posts

I agree Chicago is a great destination. It is an easy drive for a weekend trip from where I live, so I have been several times and always look forward to going back. Always lots to do there. I like to stay in River North, leave the car in hotel parking and go on foot and public transportation from there. I did go one year for the Christmas market, and while it was probably a nice Christmas market, it was way too crowded on the weekend to enjoy. The rest of Chicago at Christmas was great, though.

Posted by
908 posts

My kind of town! Love this city and lived nearby for a few years in the late ‘90s. Oh, the department stores and Marshall Field’s! The architecture! The food! Walking back from the lake in the freezing cold with snow pelting our faces! This is the stuff of dreams.

Posted by
3571 posts

If you're there over the holidays, Macy's is opening the Walnut Room !

https://chicago.suntimes.com/taste/2020/10/5/21502358/macys-walnut-room-great-tree-holidays-meal-kits-reservations-delivery-pick-up-service

As a young child and into my late teens, this was a Holiday Tradition.

I still love this city, but it has changed greatly in the past 2 years. Have spent every 2 weeks
Up there for the past 3 years for my daughters cancer treatment. The changes have been very noticeable.

Posted by
2837 posts

I've enjoyed my visits to Chicago, but would never go in the winter. The first time I went, it was late March and it was snowing and there were Easter bunnies in the store, which I had difficulty comprehending-snow is supposed to go with Santa! Of course, I've only been near a white Christmas once in my life and it didn't snow at our house, just in another suburb a little north of us.

Posted by
1915 posts

The best restaurant meal I've ever had is in Chicago (Joe's), best baseball stadium I've been to is in Chicago (Wrigley), the architectural tour is very interesting. I always have a good time in Chicago.

Posted by
3158 posts

I spent the first 21 years of my life in Chicago, including ages 18 - 21 getting my B.A. at the U. of Chicago. I agree that it is a fabulous city for museums, architecture, and food. It has cultural amenities equal to any in the world, and there is plenty of natural beauty nearby. Its only downside is an awful climate. Winters are long and brutal, and summers can be, too. We used to joke that spring and fall were lovely, but each was only two weeks long. If you go, your best bets are late May and early October.

Posted by
6857 posts

But some love cold weather. I've seen tourists here downtown on Xmas day at the outdoor ice skating rink off Michigan Avenue when the temps were well below freezing

Posted by
843 posts

I was born in Chicago and I tell everyone it was a great place to be raised. All the sports all the music all the museums all the parks and now it's one of the best places for cycling. I miss it Chicago and would move back if it weren't for this darn work thing :)

Posted by
3236 posts

I think it has been underrated big time for a long time.

I think it’s a winter thing. For the thermal clothes challenged, any place that may be frigid for some of the year drops off the tourist radar for all of the year.

Posted by
126 posts

I have only been to Chicago once, on a four day visit, but it is a terrific city, and I look forward to another visit and showing it off to my hubby. I haven't seen the "Bean", Wrigley Field, or taken an architecture tour with a boat ride on the Chicago River. The Field Museum, Planetarium and Art Institute deserve a second and longer visit than I had before. I know Marshall Fields was sold, but I do hope they still have their giant Christmas tree and decorate their windows for Christmas. When I was there before, Paddington Bear relived his adventures in their windows. And it is so cosmopolitan to meet a friend under the clock! Next visit I hope to be able to attend some theater there. Congratulations to Chicago and all her inhabitants on the Conde Nast distinction!

Posted by
126 posts

A postscript to me entry. Let's hope the Chop House is still going when things reopen. I hear they are well worth the splurge, and how "Chicago" is it to enjoy a great steak?!

Posted by
2837 posts

For some of us, no amount of thermal and other warm clothes is enough when the temperature is in the 20's-and I am aware that Chicagoans would sometimes consider 20's to be warm.

Posted by
3557 posts

My best friend is from and still lives in Chicago. I've always loved going there.

I went through both the lists and was pleased to see Santa Fe in the small towns group.

Tucson, where I live (near) now is #9 on the large cities list. And where I was born and grew up, San Antonio, was #5.

It was fun seeing the choices on the list and reading a bit about each. All are unique and special in their own ways.

Thanks, Jazz+

Posted by
6857 posts

The music never stops here I was in the music industry here for 15 years going out 5-6 nights of week even in cold weather having a good time in doors in the clubs. I met Sir Anthony Hopkins the actor when I worked at Virgin Megastore and he said "great city".
The auto show is here in the winter in February attracts a lot of tourists.

Posted by
126 posts

I’m so glad I live here, I moved from a small Texan city to Chicago and wouldn’t trade it for anything. I only been here less than 2 years and every day I discover something new. Of course the pandemic has been hard on all of us but still, this is a great city.

Thanks for the link Jazz+Travels.

Posted by
4524 posts

Another cheer for Chicago! It most certainly is a world-class city with its architecture, museums, restaurants, culture and sports. The setting along the lake and with the river (and its bridges) snaking around the Loop makes it pretty unique amongst American cities. It is big enough to have all of those draws, and yet not so big that it is overwhelming. And while the Loop/lakefront gets most of the tourist attention, the neighborhoods and historic suburbs are the gems for insiders.

I moved here in the '90s and the positive changes and developments that have occurred over the past 25 years are really incredible.