Chicago in January

I lived downtown and loved being there all year. The sky tends to get gray in wintertime but there is so much to do inside!
I never tired of walking around the city and enjoyed the museums, shops, restaurants.
Maybe you could get tickets to a Chicago Bulls game. Visit the Fulton Market area. Lots to explore.
Your wife can easily take the train from ORD to downtown on the days you are in your conference.

It's been a few years, but I've been there several times in January, and I will warn you about not just the cold, but the wind. We were blown off our feet walking around the Mile because of the wind whipping around the tall buildings. Still, it's a great city, and like most big cities, is alive with things to do even on winter. The art museum is always worth it (wait, I forgot this was Allan asking - never mind🙂). Lots of ethnic neighborhoods with food options. They have a German style Christmas Market downtown (I hope they still do), so thats one thing. Check out the Michigan Avenue underground area (where the Billy Goat Tavern is, if you're of a certain age.)

Tourists come here year round and have a good time indoors and outdoors e.g. ice skating by Millennium Park. Everything is open and the stores have clearance sales before doing inventory.
The Art Institute will have this exhibit https://www.artic.edu/exhibitions/9344/the-language-of-beauty-in-african-art
Buddy Guy (octogenarian blues musician that influenced Led Zeppelin, Clapton the Rolling Stones) usually plays the whole month of January at his namesake club.

@stan
They do call it “The Windy City.”
Joking aside, appropriate gear helps a lot. Being from Canada, I assume Allan understands winter and has the clothes to withstand Chicago weather. So many attractions are indoors, there should be no shortage of things to do.

My understanding of winter is the prime concern for my question. I've never taken a winter vacation to another winter location before and struggling with the thought of it. If the Blackhawks were in town, the decision would be easier, but the Travel Gods decided it would be funny to send them to Calgary at the same time I'm in Chicago.

By the way, did you know there is more than one theory how it got named The Windy City? I like this story better. https://www.history.com/news/why-is-chicago-called-the-windy-city

The art museum is always worth it (wait, I forgot this was Allan
asking - never mind🙂).

Stan, maybe you could loan them your Dogs Playing Poker in Velvet for while I'm there. I'll pay to see that.

I have only been to Chicago in the summer, but we enjoyed the museums and dining out at some wonderful restaurants. There are several regular forum posters from Chicago, perhaps you could reach out and arrange a “meet-up”. I have done meet ups in Chicago, Tacoma and Paris and they have all been a huge success.

The political windbags theory about calling Chicago the “Windy City” is what I heard when living there.

Your wife could also go into Chicago on the Blue Line train while you are stuck at the Hilton. It goes from the transportation center on the back side of the Hilton, and even has an underground passage from there, so she will not have to go outside until she gets to Chicago city center.

There's a bus from downtown to the Museum of Science and Industry (MSI). That's a full day. The Field Museum of Natural History, the Shedd Aquarium and the Adler Planetarium are next to each other. Though it's undoubtedly a cold walk on the lake shore, there's a bus (again from downtown) that goes to all 3. The Field can fill a full day, Shedd and Adler - maybe 1/2 day each. The tall buildings and straight streets downtown do create wind tunnels that I found very cold last month.

Maybe stay "near north" - tons of restaurants/nightlife, not so windy, and you can take the el downtown to get the museum buses.

Has anyone been to the Chicago History Museum? Local History museums are usually our favourite. We've been to the Field Museum and it was OK, but not the type of museum we usually seek. As an example we liked the British Museum in London, but loooved the Museum of London. The planetarium is a good thought, we were fascinated by Griffiths Park Observatory in Los Angeles.

We went to the Chicago History museum on our visit. Information about the Chicago fire and various food items from Chicago. We both thought it was an “ok” museum, but not a must.

Lived in the 'burbs as a kid, and went to the city many many times.

Art Institute is a wonder. If you like art, this is your place to go. The Oriental Institute is a wonder for in-depth middle-east archeology and history - not real big, but that's where a lot of actual discoveries were made. There's also a Frank Lloyd Wright house in that area. Lincoln Park zoo is not worth seeing. But the Lincoln Hotel near the zoo is fun - we had oysters and prosecco - oysters on sale. I just checked - you can get a room there for $95/night, which seems pretty reasonable, considering it is the near North, and right next to Lincoln Park. Maybe transfer there for the end of the trip?

Chinatown has a number of great restaurants. We are partial to dimsum restaurants. There's one that we go to a lot - don't know the name, but it's on the second floor of a corner restaurant. The space is huge - 60 tables - all with Chinese folks. Imperial restaurant. We've been 5-6 times.

For Chicago hotdogs, there are a TON of places. We love Portillo's which is a chain. Also Chicago deep dish pizza is great. You gotta have the Chicago hot dog, the Italian beef (essentially a French dip with peppers) and fries. SOOOOO MANY CHOICES IN THE WHOLE AREA.

Rick Bayless, the high-end Mexican chef, has several restaurants in downtown Chicago in the Loop. Topalabampa is the main one - you need reservations. There's also the Russian Tea house (RUN BY UKRANIANS) and Berghoff for traditional Bavarian food - I love this place. In the Loop area, there are a TON of old bars and taverns that are mostly lunch-time trade.

All of these tips make me want to hit Chi-town again.

You'll be at the O'Hare Hilton - not far from Arlington Heights (where I grew up) - there's a number of good Italian beef restaurants on Arlington Heights Rd - Johnnie's Beef - get the double dog and fries. There's also a Japanese supermarket at the corner of AH Rd and Algonquin, which has 6-7 Japanese restaurants which are really fun. Mitsuwe Marketplace. Good Irish restaurant in AH,

I've been to Chicago any number of times but one of my favorite visits was in early January with my sisters. The Christmas crowds were gone and there was still a lot to see and do.

I'm partial to the Museum of Science and Industry; especially because it holds the exquisite Colleen Moore's Fairy Castle (a miniature fairy castle in 1:12 scale commissioned by silent movie star Colleen Moore). You may not be interested but it would probably be something your wife would like while you are busy - it's easily reachable from downtown and is amazing!

The Christkindlmarket might still be open if you're going in early January, along with other Christmas exhibits (including the tree)

Girl and the Goat is a great restaurant to try - very innovative and wonderful. Don't limit yourself to Chicago deep dish pizza - the city has an incredible array of excellent restaurants.

I was annoyed to find Chicago museums that charged up to $3 coat check fee, which is a problem in the winter. (However, many museums closed their coat checks during the Pandemic.)

It's also a problem that so many (Chicago Style?) buildings have exterior ornament that can ice-up. There are roped-off sidewalks everywhere, which is antithetical to the joy of urban strolling.

It is a real dining town, but reservations are essential. The airport is famous for winter weather delays!

Note: I've been three times in 20 years, and love it.