Please sign in to post.

Chicago Mini-break October 2023

As companion to my April trip report about New York, here's a trip I took last week to the other American city with a large collection of skyscrapers.

Had only 3 days to play with, it's a 6 hour drive or an hour flight, so flew with the short time frame using Southwest points.

Thursday: Flew into Midway airport arriving about 10:30am. Normally we are transit people so took the convenient orange L train into the Loop (downtown). Boston has the T, Chicago has the L (or is it el?). Like NY they accept contactless credit cards for the train so no need to buy tickets and all that, just tap and board, so simple. Train was clean and comfortable, and not crowded, a big thumbs up. Arrived at Hotel Blake, a boutique newer hotel, about 11:30 and were allowed into the room, very nice room and a good price too. This is a South Loop location, when I lived in Chicago 45 years ago this was a dicey area, but now full of pedestrians and a fascinating collection of new and old buildings, and "hip" for lack of a better word. Noticed how spiffed up the city looked and the almost complete lack of homeless, all the more striking to me because I was in Anchorage last month and the homeless are pretty prominent there, unexpected that a metro area like Chicago, maybe 25 times bigger, has such limited homeless visual impact to visitors. Almost no graffiti also, all in all a really a handsome city. Like New York, the last 45 years have been kind to Chicago and both cities have never been better.

It was raining and the Art Institute was open till 8 on Thursdays so went there. I was there 45 years ago and impressed, but now having seen museums all over Europe I am even more impressed with this museum's collection. Fabulous collection, especially the French Impressionists, better collection than Orsay if my memory is correct. Spent about 4 hours which is about my limit for museums. Noting that I have visited the other big museums, Field, Science and Industry, and Shedd on other more recent trips but skipped the Loop area those times. Chicago has an amazing collection of big, high quality museums, maybe exceeded by only New York and London.

Posted by
4510 posts

Thursday evening splurged on a fancy restaurant in Fulton Market called Rose Mary, which serves food by plate: zucchini fritters, tuna crudo, bucatini, Croatian bread, scampi. Took the L both ways, no issues.

Friday decided to walk around the Loop and enjoy the old and new buildings, and the monumental public art. Found a print architectural walking tour online and walked into several of the world's first skyscrapers, from the 1880s, interesting to see and walk around (allowing the public to prowl around private office buildings isn't something that would be allowed in New York), lots of great details, relief sculptures over doors, extensive mosaics of historical events, metalwork, interesting. Sometimes there would be an historical handout for free sitting next to the guard desk. Occasionally we would run across a walking tour but mostly it was a day of self-directed discovery, the kind of travel I like best. Repeating how tidy the city is, and busy with people. Walked up Dearborn to see the 3 huge artworks, a metal sculpture by Picasso, another by Calder, and an enormous mosaic mural by Chagall, all apparently gifts to the city by the artists. Dinner was at a Oaxacan restaurant in the Uptown area, Kie-Gol-Lanee, a bit far but still took the L both ways, no issues. The concept of a chocolate sauce (mole) sounds so fantastic in theory but always ends up a disappointment to me anyway when delivered on the plate.

Posted by
4510 posts

Saturday we booked the Chicago River boat tour done by the Chicago Architecture Center, a bit pricey including the museum, $70 but wonderful, the docent was knowledgeable and filled the 90 minutes with good information. It is hard not to be impressed by the quantity of tall buildings, seen from the river and set back appearing even more majestic. I don't know when the Riverwalk was completed but I was bowled over by the size of it, about 2 miles of continuous bars, food trucks, live bands, full to brim with Americans, Europeans and Asians enjoying the open air setting and the sight of the river with the tall buildings all around. It was chilly but everyone was out enjoying it all. I really had no idea Chicago has this international party going on, much like New York has.

Finished the day spotting a couple Tiffany Studio domes, at the Chicago Cultural Center and then over one of the atriums in the old Marshall Field's store (Macy's now), then took the L (of course) back to Midway for an evening flight. Had boarding position C48 yet got an aisle seat in row 3 with bin space, a perfect ending to a great trip.

A final thought: if you want walkable cities, great public transport, great food, an outdoor party atmosphere, and great art, there's no requirement to go to Europe, either Chicago or New York will substitute well.

Posted by
3835 posts

Thanks for the trip report. Very enjoyable. I was in Chicago for a long weekend about 25 years ago -- stayed in a friend's brother's partner's apartment. He was a professional chef -- amazing food. The whole trip was a lot of fun and included the Second City comedy troup. About 10 years ago, I took a day trip on a cheap Southwest fair from Louisville to catch a Cubs/Reds game at Wrigley Field. That was a lot of fun, too. In the latter case, we walked past a street of destruction and overturned cars. One of the Transformers movies was being filmed.

Posted by
11133 posts

What a wonderful report about a favorite city of mine! I loved living there years ago.

Posted by
6274 posts

Nice report, Tom! I love Chicago! I used to visit quite frequently when my sister and a brother lived here. And I lived here when I was 3 years old (don't think that counts, though). 😊

I do love the city, though, and it was great fun to read your report. I will have to get back there in the near future. Thanks!

Posted by
156 posts

Thanks for the report! Makes me want to check the Art Institute again after many years of absence.

Posted by
2288 posts

I have 3 favourite midwest cities - Chicago, Detroit, and Minneapolis with Chicago likely edging out the the other two, for top spot.
.
I remember being in Chicago on business in the early 90s and having to blow-off a meeting for health reasons - reason being, the Cubs were playing an afternoon game at Wrigley Field.

In those days afternoon games were pretty much the norm, today they have night games, but a limited number [By-law].

Posted by
4078 posts

Chicago is always a good idea if you're looking for a place to go. It was the first place I'd been that I really noticed architecture.

Posted by
2490 posts

My husband is from Chicago so we have been numerous times most recently in September. It was fun to read your impressions.

Posted by
7811 posts

if you want walkable cities, great public transport, great food, an outdoor party atmosphere, and great art, there's no requirement to go to Europe, either Chicago or New York will substitute well.

Yeah you got the public transport right I have never owned a car and rent my parking space out; but since we live here and are big city folks we prefer the pedestrian only streets prevalent in Europe over New York, given the current anarchic way people drive in Chicago and in big American cities.

Posted by
1361 posts

Thanks Tom! You made me homesick. I’m a Chicago native who started taking the L by myself when I was about 12. Would meet my friends and head to Grant Park or in the summers, go to the Art Institute on its free days, Saw the Boss at the Grant Park band shell. I need to go back.

Posted by
4510 posts

we prefer the pedestrian only streets prevalent in Europe over New York

Have you been to New York recently? There are new pedestrianized areas, the Wall Street area is closed to traffic, and Times Square is closed to traffic. And there's been a proliferation of bike lanes, and with the dining sheds built in the street (below the curb in former driving lanes) during covid and now being left-- all this has flipped Manhattan from vehicle-dominated to pedestrian-dominated.

Chicago also has put in bike lanes (admittedly lightly used), and I saw at multiple intersections the "all-red" traffic light signal timing (which I have only seen previously in Montreal), where all directions of traffic are stopped and then pedestrians can cross all the streets at once (even kitty corner, since every leg is stopped for pedestrians)-- I thought that was pretty innovative, maybe it occurs in Europe somewhere. No city is as dangerous to walk in as Rome, I was knocked down exiting a bus at a stop because a scooter had tried to pass a stopped bus between the unloading bus and the curb (?).

Posted by
7811 posts

We also prefer Europe for more affordable fresh cooked and baked goods the non tipping culture and less aggressive panhandling and unfortunately people with uncontrolled mental illness or addiction to opioids wandering around.

Posted by
4510 posts

You must have a certain European country in mind. My last trip was full tipping culture (Germany, Czech Republic, Hungary) to the penny the same as the US, all three. Also plenty of mentally ill homeless, in Prague at least, despite free services available on request.

The US has generally become more expensive lately, that’s true.

Posted by
7811 posts

I was in Prague in May all I noticed was grifters trying to sell currency. I have lived here since 1969.

Posted by
119 posts

Thanks so much for your report! It makes me want to plan a weekend in the city. I'm only 45 minutes away but really haven't been there in a while :)