@SJ2727 What sort of things do you like seeing? Architecture, parks, museums, zoos, old neighborhoods, coffee shops, or something else? The Loop is, of course, the most central place, because, among other things, you have access to all the L lines, as well as to the Metra, and you are not to far from the Amtrak trains. Of course it is expensive, though not as expensive as the Gold Coast.
All of it! well, except the zoo. lol. Thanks.
@SJ2727 Mag Mile is just a stretch of Michigan Avenue mostly with stores you can find anywhere (Nordstrom, Gap, etc). I don’t think it’s the thing to see but, if you’re walking between sites, you could walk down Michigan and see it.
I would stay near Mag Mile, though, because it is central to most downtown things you may want to do. Top Chicago worthwhile things to do?
- Art Institute of Chicago
- Maggie Daley Park
- The Bean
- Check out any concerts in Millennium Park
- Boat Architecture Tour
- Lincoln Park Zoo (free! just north of the city in the Lincoln Pk neighborhood)
- The Lakefront (rent bikes or walk from Maggie Daley Park north to North Ave beach)
- Deep Dish Pizza (so many options - I would google and then decide)
- Museum Campus (but only if you have a rainy day or want to be inside, includes Planetarium, Field Museum, Aquarium - all amazing but summer in Chicago should be spent mostly outside if it's nice!)
- Top of the Willis Tower (Sears Tower!!)
- A Cubs game!!!
I would not stay in “the loop” as it’s the business district just west of Michigan Avenue and the lake. I would stay as close to the lake as possible as that’s where most of these sites are and you will have no reason to even have a car.
If you’re staying in the Loop, Millenium park, Grant Park, and everything in them (the Bean, Buckingham fountain, etc) are within easy walking distance. There are a lot of shows in the Pritzker Pavilion over the summer as well, and there is Summer dance in Grant park (different bands and different style dancing outdoors).
There are a whole bunch of theaters and other venues in the area, like Harris Theater and The Auditorium Theater. Check out what is playing there.
There is the Art Institute and its Museum, the Chicago Cultural Center, a lot of great buildings, the Chicago River Walk, and so much more, and this is only in the Loop area. You could take an architectural tour of Chicago, of which the best are on boats.
If you walk up to the Miracle Mile, and then into the Gold Coast, there are a lot of high end stores, the Water Tower, the John Hancock Building (you can have a drink at Bar 94 or something to eat at the Signature Room). You can see the Wrigley Building, the Tribune Tower, grab a cheezborger at the Billy Goat Tavern (two stories are related to that).
If your city does not have a Chinatown, and you’re in Chicago over the weekend, go to Chinatown for dim sum.
That’s enough for now. Hopefully other Chicagoans will add stuff.
@SJ2727 Ha. Just saw your “no zoo” comment. But Lincoln Park Zoo is just part of awesome Lincoln Park. It’s like Central Park Zoo where you can just walk through. Right up against the lake so you can hang at the lake, get some ice cream, walk to the zoo - it’s all near each other just north of downtown. The zoo also has swan boats that you can take out and pedal yourself and get the BEST view of the city just a few miles away. It’s a really nice place to be for an afternoon. Photo ops everywhere you turn.
Lincoln Park Zoo is also free entry - one of the very last free zoos in the USA.
Now I want to go to Chicago!
D26 obviously has a way to go to decide but has expressed some interest in architecture, so the boat tour sounds excellent. When I was there last I visited the Robie house near the university - it being long ago I don’t remember if it was particularly out the way? U Chicago is beautiful of course.
UChicago is in Hyde park, which is a 25 min drive from downtown, if LSD is not jammed, and it can take a lot longer if it is. You can also catch the Metra from Millennium Station which stops not far from the university. It’s a 14 minute ride, but that does not include the wait. Hyde Park and the University are great places to visit, especially if you like visiting book shops.
if you go down to Hyde Park, you can also hit the Museum of Science and Industry. It’s very close to U of C and you should go on a Robie House tour as well. Frank Lloyd Wright rules!
We will actually be coming in on Amtrak - taking the California Zephyr. There was much debate about whether to get off in Denver and fly the rest of the way or just stay on the train, but in the end we decided to go the whole way. I think after 50 hours on the train we will be itching to go for long walks and open air boat rides haha! Really looking forward to train ride though. At least the first part of it, lol. Feedback we have from others who have done it is “it’s something you must do, but you must only do it once” :lol:
@SJ2727, we used to love taking trains across the continent! One of the things we truly miss, what with having moved to Alaska (where there’s no overnight trains). Have to get a sleeper, though, which always made us wince when it came time to pay.
@dfbdfb thats why we have booked already - the family sleepers sell out fast. We got the last one on our preferred date.
@SJ2727 My brother did that trip in reverse, except he went all the way from Boston to San Francisco! He said Boston to Chicago was boring but he loved Chicago to SF! And now you are making me want to go to Chicago too. We have good friends outside the city and haven’t been in years.
A bonus: There are some pretty spectacular parts of the California Zephyr run that are effectively impossible to see any other way than by train, and Amtrak tries to time things so that you’re in daylight for them.
@SJ2727 We took the Desert Wind/California Zephyr train with a sleeper in 1995 when we came for grad school - my parents live in LA, so we flew there and sent most of our stuff, and took the train since we had too much luggage to take on a plane.
It was amazing. The scenery, the atmosphere, etc. From sitting in the observation car to not meeting new people in the dining car during meals, it’s absolutely worthwhile doing. I am a little jealous, as a mater of fact 
The Desert Wind ended in 1997, though, which is too bad, since now you can only take the Southwest Chief if you want to go directly from LA to Chicago, and that route isn’t as nice (I’ve driven it a couple of times).
PS. we were supposed to take The City of New Orleans from Chicago to Urbana, but the train was 3 hours late, and we ended up taking a Greyhound. That leg of the trip ended up in many adventures, but those are different stories for a different time. Suffice to say that it was the Great Heat Wave of 1995, and Greyhound did not yet have a station in Union Station, so we had to walk to the main Greyhound Station on Harrison, and that was just the start.
That is indeed the incentive to spend 51 hours by rail rather than 4.5 hours in the air 
very much looking forward to that. I’m just hoping it’s not too difficult to get seats in the observation car.
I hope you have a good train trip. Our two round trips have been less than ideal. Not all of it Amtrak’s fault, but we’ll never do it again.
When I was backpacking back in the days of yore, I took many a long distance trip on Amtrak with my rail pass. Recently have done a number of shorter trips (Anaheim to San Diego, and the DC/Philly/NYC/Connecticut routes. Never really had any issues. This will however be the first time in a sleeper ever on Amtrak, and since I did an overnight Amsterdam-Berlin route, also many years back. Sorry to hear your experiences were not great. I had specifically asked some locals who’ve done this route, and they all recommended it (but again, recommended doing it only once!)
Also we will definitely fly back not do the reverse again!