After wanting to do it for 20 years and not being in a financial position to do it, I’ve finally bitten the bullet and booked a long-distance Amtrak trip with a sleeper. I’ll be hopping on the Empire Builder in Seattle for a 2-day ride to Chicago in late April, then staying 4 nights at a decent hotel in the Loop before flying back. This is one of those kind of trips where the trip is as important as the destination, so I haven’t really put much thought yet into what I want to actually do in Chicago aside from going up to the top of whatever the Sears Tower is these days, getting some deep dish pizza (yes, I know you guys prefer thin crust, but I want a ginormous mountain of pie that I can take to my hotel room and consume over the course of my stay), eating an Italian beef sandwich, and seeing that giant bean and the Museum of Science and Industry.
My train pulls into town just before 5 PM (if it’s on time, and that’s a big if as far as Amtrak is concerned), so my first night is likely going to be confined to checking into the hotel, getting something to eat, and stretching my legs after being confined in the big metal stink tube for 48 hours. I’d eagerly appreciate any ideas from locals or frequent visitors as to what must-see attractions I’d be a fool to miss or where to eat that’s good and not just a tourist trap or where to avoid. I don’t plan on renting a car, but I’m fairly comfortable with navigating urban mass transit, and I assume there’s an app I can pay my fare with that’s pretty straightforward to use.
I’ll be arriving on a Sunday and flying home on Thursday, if that matters.
The architecture boat tour seems to fail to disappoint as a “what to do in Chicago” suggestion.
I’m a local and was impressed with it, it’s a unique pespective on the buildings, with some interesting background info. You can even get a drink on the boat.
I don’t know what kind of activities you are interested in, but I’d suggest checking out CityPass. It gets you access to up to five different museums and other things, including Willis (Sears) tower and the architecture river tour. We used it when we took our granddaughter to Chicago this summer.
We loved the Architecture boat tour (did it twice)
I never found the Field Muesum (natural history–stuffed animals) to be that interesting, but maybe it’s just me.
On the other hand, the Chicago Art Institute is a world class art museum.
I’m with you on deep dish pizza. And the thin crust. With four nights you can have two of each.
Have you eaten an Italian beef sandwich before? I’d have more than just one, even in that narrow time frame. While some places do it better than others, I think any of the city’s top 500 will make a very good Italian beef sandwich. Of course, if some top-ranked place is easily accessible or if making the trek out to one appeals to you, go for it. Otherwise, I wouldn’t bother going out of my way, because the vast majority of them are pretty good. They can be very messy, too. Keep your sleeves out of the way, and, before digging in or even ordering, make sure you’ve got napkins or whatever to wipe your hands and face.
I have done this many, many times - for the fun of it - but it takes a certain kind of personality to consider it fun. I’ve taken the Lakeshore Limited from Chicago all the way to Albany, then straight onto the Adirondack to Montreal, and THEN onto Via Rail for another sleeper to Halifax. (And I’ve made that same trip four times.) If you want to meet a lot of colorful personalities, truly see the American continent from the ground level, and you have A LOT OF TOLERANCE FOR SITTING AROUND FOR HOURS WAITING, it’s a great way to travel. If you do not have A LOT OF TOLERANCE FOR SITTING AROUND FOR HOURS WAITING, it’s not for you.
I grew up around Chicago and still have family back there, but strangely I don’t care for Italian Beef at all. Sacrilege, I know. I’d much rather get a Chicago dog (Gene & Judes!) but hey you’ve got enough time to eat all the meats. Where deep dish pizza is concerned, I prefer Giordano’s to Lou Malnati’s but you will find lots of conflicting opinions
Architecture tour really is great! All of the museums are good, depending on your interests. I go to the Art Museum once a year when I’m in town visiting. Natural History museum is huge and easy to get lost in but I think the temporary exhibits can make or break your visit. We went to the Chicago History Museum for the first time last year and even that was entertaining, so it’s tough to go wrong if you want a little ‘culture.’
Of the tourist traps to avoid, really the only one that I’ve never understood is Navy Pier… but even that might be worth doing the one time just to see what it’s all about.
The CTA, as well as the suburban Pace (bus) and Metra (train) systems, uses a system called Ventra for fares. It looks like you can set it up to work on your smartphone, or buy a Ventra card at a station.
I’ve been to Chicago maybe 8-10 times, it’s a great city to visit.
Some of my favourites:
Art Institute, especially the Chagall windows
Boat tour
Oak Park (Franklin Lloyd Wright) tour
Walking up the Miracle Mile into Gold Coast/Old Town
Millenium Park (obv. weather dependent)
My favorite museum has always been Science and Industry, but my wife prefers the Shedd Aquarium and my (adult) kids prefer the Field Museum. The Brookfield Zoo is great, but it’s not conveniently located and you really need several hours to do it right.
No one here has discussed nightlife, but with Second City, Blue Man Group and an excellent theater scene, you should definitely explore entertainment options.
Our last visit was pre-COVID, but we enjoyed the Hancock building (I’ve heard it had better views), Lou Malnati’s pizza (walking distance to Hancock), the Art Museum, Field Museum, and Science and Industry Museum. We gave up on Uber or Lyft since cabs are easy to get and affordable. You might also want to see what touring Broadway shows are in town.
Just a note on Chicago museums, and their proximity to each other:
The Field Museum, the Shedd Aquarium, and the Adler Planetarium are all part of the “museum campus,” which is just southeast of the Loop, and all three are within easy walking distance of each other.
The Art Institute is on South Michigan Avenue, in the Loop. It’s about a mile and a half from there to the Museum Campus.
The Museum of Science and Industry is in the Hyde Park neighborhood, about seven miles south of the Loop.
The Museum of Contemporary Art is north of the Loop, in the Streeterville neighborhood, near the Water Tower and 875 North Michigan Avenue (the building which Chicagoans will call the Hancock Building until the end of time, but which formally lost that name a few years ago)
Many of the Greek restaurants I used to visit when in Chicago are gone but the Athenian Room is still there. Go there if you like Greek food or if you want to learn to love it like I did.
I got very nostalgic reading this thread. When I was in college my roommate was from Chicago and we spent a lot of wonderful weekends there. I would love to visit the Art Institute again. And have some real, authentic deep dish pizza. I hope you have a wonderful time.
Italian Beef (Portillo’s, Al’s, or Johnnie’s. Might as well grab a hotdog too)
Museum campus (although science and industry is my single favorite museum)
Architecture boat tour
Improv
Sears Tower sucks. Absolutely do not wait in a 2 hour line (a real possibility) for that shit. Hancock has a restaurant. Grab a drink there instead. Or do neither.
Cindy’s bar on top of the Chicago Athletic association hotel has a great view too
Kuma’s corner is a great burger and a fun atmosphere
Blue’s is going out, but you can still see a show at Rosa’s
And for good measure I asked ChatGPT for 5 things to do in Chicago that not everyone else would recommend:
Visit the Museum of Contemporary Art, which showcases a diverse range of contemporary art from around the world.
Visit the Garfield Park Conservatory, a beautiful botanical garden with over 200 species of plants.
Take a boat tour of the Chicago River, which offers unique views of the city’s architecture and history.
Visit the Chicago Cultural Center, a stunning Beaux-Arts building that houses a variety of exhibitions, concerts, and events.
Visit the Chicago Magic Lounge, a unique entertainment venue that showcases the art of magic and illusions.
So far I’m hearing good things about the boat tour, so I think I’ll definitely pencil that in. The Citypass sounds like a good deal and includes a few of the things I want to see, so I’ll probably go for thay as well. (I had no idea Citypass was a franchise - Seattle has one too.)
There’s a Giordano’s near the hotel, so I think I’ll go there for pizza - I saw the one in Vegas when I was there this year but skipped it because I already had a dinner reservation, but that pizza looked delicious. I’ve heard of Kuma’s and I’ve looked at their menu online in the past, so I’ll probably check them out too.
What kind of weather should I expect in late April?
A friend of mine has been a docent for the Chicago Architecture Foundation for years, and has worked on the architecture cruise many times – she highly recommends it.
For what it’s worth, Giordano’s thick pizza (“stuffed”) is slightly different than the original “deep dish” style (Pizzeria Uno, Lou Malnati’s) - the primary difference is that stuffed has a layer of crust on the top (hence, the toppings are “stuffed” in between the top and bottom crusts), while deep dish just has a single layer of crust at the bottom.
In the end, they’re all delicious, and very filling.
We briefly had a Chicago style eatery in Olympia that did Italian beef and deep dish pizza, but they went out of business years ago. I’ve made a crockpot version at home with a seasoning mix I found on Amazon, but I’m eager to try the real thing.
