Chicago: what to see/do and where to stay!

It is possible to stay near the lake and see art museum, zoo, and take mass transit out to see the Frank Lloyd Wright stuff and Hemingway house in oak park. It's been 10 yrs or more since I did that trip w 3 friends, so my hotel recommendations are outdated.

The Field Museum…

You can both get to the Loop, on the Blue line from O'Hare, on the Orange line from Midway.

I am partial to hotels around the river and Michigan Ave. Kimpton Monaco, Royal Sonesta, Club Quarters are few I've styed at, usually cherry picking one with a good rate. The Emerald Loop is right there for late night dining. A lot of hotels in Chicago are in late dining deserts.

The Chicago Architecture Center is nearby and I highly recommend one of their boat tours.

Art Institute of Chicago is worth a few hours. I like The Gage, across Michigan Ave one block north. Otherwise not much of a foodie. I see food and I eat it.

Farmers markets don't start until June.
Stay near Michigan Avenue and Balbo street if you can afford it. You can access the lake for a run and great museums (Art Institute, Adler Planetarium, Field Museum, Shedd Aquarium) on foot or by short express bus ride from there. Take the #6 or 10 bus south bound to the Museum of a Science and Industry from Michigan and Balbo . From the Museum of Science and Industry walk west along 57 the street to the U of Chicago campus. You will find among the best independent bookstores in the country: Powell's (used bookstore), 57th Street bookstore and Seminary Co-op next door to Frank Lloyd Wright Robie House:
https://www.flwright.org/tour/robie-house

Also time permitting, visit this museum nearby: https://isac.uchicago.edu/ on the campus of U of Chicago.
Other places to check out :
Garfield Park Conservatory (take the Green Line elevated train from downtown to get there): .https://garfieldconservatory.org/

Chicago is one of the great walking and public transportation cities. You can also rent a bike and ride the paths along the lake adjacent to the jogging paths
For deep dish pizza try Lou Malnatis or Pizzeria Due.
For authentic Asian you can either catch the Red line train south to Chinatown Cermack or north to Argyle which has a collection of Vietnamese, Thai, and Cambodian restaurants. There is also a Little Italy and Greektown restaurant area all accessible by public transportation.
For the Live music night scene the roots of rock n roll aka the Blues can be heard at Buddy Guy's Legends blues club at Balbo and Wabash street.

Excellent choice! I've stayed several times at Hotel Blake on Dearborn St. The rooms are spacious, comfortable and modern, with small fridge and microwave. It's a block or two from the el and bus lines. It's walking distance to all Loop locations and safe at night. It's about a 10 min walk due east to Grant Park, cross it in 3-4 minutes (via Buckingham Fountain) to the lake.

My favorite spots:
Art Institute - one of the finest art museums in the world, especially for Impressionists. Check for temporary exhibits. Don't miss the miniature rooms on the lowest floor. Just a few meters away is the Russian Tea Time Restaurant. A great place for lunch (you'll probably need a reservation on the weekend). Try the afternoon tea & samovar service (I believe it's owned/run by Ukrainians).
MSI Museum of Science and Industry. There's a bus from the Loop. It's an all-day experience so you may not want to spend a whole day there, and not really worth going for less than that.
Field Museum of Natural History is part of the "museum campus" which also includes the Adler Planetarium and the Shedd Aquarium. You could easily spend a whole day seeing them - the Field will take the most time.
Hancock Center used to be the tallest building in Chicago. It's on North Michigan Avenue and has the best views of the city, especially the Loop, because it's the only building with an observation deck outside the Loop. Sadly, the free views from the 95th floor restaurant (and toilets !!!) closed a few months ago.

I tend to agree with Sam for hotel location. Many locals will recommend the River North area. Many hotel choices, many price levels. I'm personally less a fan of Loop and south Michigan Ave hotels unless here for a convention. Lots of hotel reviews available online for all areas suggested.

No argument intended with other suggestions above. Just my opinion - OP can decide what fits their needs.

Rose, I hope you don’t mind me tagging along. My trip to Chicago is coming up at the end of April so I’m also interested on tips for activities. Does anybody have thoughts on the comedy venue called Second City?

I used to spend a lot of time there. Lots of interesting ethnic neighborhoods. I liked to visit Gene's Sausage and Deli in Lincoln Square (Polish sausage), and if you're old enough to remember, the Billy Goat Tavern under Michigan Avenue (SNL cheezborger, cheezborger, Pepsi). Neighborhood festivals in towns on the Northside. Oak Street Beach park. Lots of historic places if you dig deep enough into history.

Second City, was the starting point for a lot of future stars whose names you would recognize.

In addition to the boat tours, the Chicago Architecture Center also offers walking tours with various themes. I took two and I really enjoyed them. Check the schedule on their website to see what is offered during your visit.

We stayed at the Royal Sonesta Chicago Riverfront last December - very nice, very central. We walked and Uber'd everywhere, no problem. Loved the Art Institute, and definitely look into Second City if you like improv. We took a fun Gangster Tour via Viator, about 1 1/2 hour bus ride with several hop-offs to see historical places. We splurged on a fab steak dinner at Smith and Wollensky Steakhouse - that city has the most amazing food (including a macaron/dessert vending machine in a random brick wall near our hotel.) And of course don't miss your photo op at Cloud Gate (AKA the Bean) in Millennium Park.

Have fun in my home town!

The CTA's blue line from O'Hare and orange line from Midway are easy economical options, but if you are traveling at night, I would not recommend it. It sounds like you are each getting there alone, and after the daytime crowds thin out, I would not be comfortable, especially from Midway.

In terms of hotels, do you want to be in the middle of the action, which would be more by the river or in a quieter area on the edge? I love the Drake which has a more elegant ambiance but it is not trendy in the least. It is right on Oak Street Beach and you can pick up the the running paths along the beaches right there and many rooms have Lake Michigan views. I realize many would consider this stuffy, but I like the quiet.

The Architectural Boat Tour is a must, but don't book it yet. You would be able to get tickets the day before at this time of year. You need to watch the weather, it snowed there today! And Second City is hilarious, most of the original cast of Saturday Night Live started there and you would recognize many of the alumni pictures.

I am not a fan of a lot of the restaurants in the Michigan Avenue/Downtown area. I think they can be overpriced for what you get and boring. But if it is important your restaurants be nearby, you have a lot of options.

If you are foodies, that whole Fulton Market area is full of award winning restaurants, and a fun vibe with the streets closed off and outdoor seating. There, we love Rose Mary, Monteverde, Ana, and Beatrix. Stephanie Izard , the first female winner of Top Chef, got this area hopping, with her Girl and the Goat and our new obsession Cabra, and she has others. It is worth an Uber ride to try one of these, but get reservations yesterday!

Rick Bayliss's Topolobambo is also good. It won James Beards best restaurant of the year when it opened. It is attached to his Frontera Grill which has similar food but is more reasonably priced. The Kitchen is a pretty spot along the river that has great views, it might be good after your boat tour.

For a different experience, take the 151 bus north and you will get a nice view of Michigan avenue, and the lake and get off at Lincoln Park Zoo. I am not a zoo person, but on southern end, the gardens and ponds there are beautiful, and the zoo is FREE. The Green City Farmer's Market is right there and it is open on Saturday mornings starting in April. It is produce, baked goods and flowers only, no arts & crafts. Nearby, have lunch at the J. Parker on the top of the Lincoln Hotel. https://www.jparkerchicago.com/gallery/

London House's rooftop bar also has killer views, you definitely need reservations.
https://londonhousechicago.com/rooftop/

Enjoy!

Another vote for the boat tour of architecture!

Read about the tribune tower and the odd rocks built into its front. :)

I'm glad to see that Sunny expressed concerns about airport public transport - especially from Midway. I concur with what was said above.

Highly recommend the Architectural walking tour!

There are several of these, with various themes.

I'm glad to see that Sunny expressed concerns about airport public transport - especially from Midway. I concur with what was said above.

I took the Orange Line to Midway on a Saturday night, really nothing concerning at all on this line, and the neighborhoods are fine.

I've stayed several times at Hotel Blake on Dearborn St.

I stayed once, great hotel and attached restaurant.

I'm glad you had that experience, Tom. I am a local. I would not take the line at night. Neither would I take the Blue line at all hours. To each his own.

I would not take the line at night.

Taking the orange line into the Loop in the morning from Midway, what was astonishing was the complete lack of homeless, not anywhere visible from the L: not under the bridges, or along the river-- nowhere. And with all the people out and about Chicago feels like one of the safest US cities.

I am native since 1969 of the area of the city where they tell new transplants and tourists to never go where ironically one of the top universities in the world is located. These days I would not take the orange or blue lines after 9pm. But the Democratic Convention is coming this summer, so they have been cleaning up.

You have many great ideas suggested here so I didn't repeat them, but I do think the Art Institute is a must. If you are member of a museum in your home town, the Art Institute is part of a reciprocal programs group, you might check to see if you can get in for free.

The CTA has a 24 pass for $5 for unlimited use on the trains and buses. If you do one round trip then it pays for itself. It is 24 hours not midnight to midnight so you have flexibility with when you want to activate it. Don't buy the reloadable Ventra card because you have an additional charge for the card, buy the disposable pass.

The Art Institute is indeed a great place to visit. In planning my own re-visit, I have found out that the Art Institute is closed on Tuesdays AND Wednesdays.. just some food for thought for your planning Rose.

Hello from ground zero.

Bookstores: The best bookstore on the South Side Seminary Co-op (https://www.semcoop.com/) in the Hyde Park area near the University of Chicago. Just a couple blocks away is the also recommended 57th Street Books (https://57th.semcoop.com/). On the North Side of the city, the best is Unabridged Bookstore (https://www.unabridgedbookstore.com/).

Walking: You've come to a right place. The 606 is a rail to trail walking path on the North Side: https://www.choosechicago.com/articles/parks-outdoors/explore-the-606/. (It's twice the length and better designed than the High Line in New York, which the national media salivates over, but they miss The 606.) Another great walking path is the River Walk: https://www.chicago.gov/city/en/sites/chicagoriverwalk/home.html.html. You can connect that to the path along Lake Michigan. The path along Lake Michigan is around 25 miles one way or about 50 miles back and forth. That means you could essentially walk for two to three days if you want.

Hotels: I don't know many because I live here, but my sister as part of a business trip stayed at the very cool Chicago Athletic Association Hotel on Michigan Avenue: https://www.chicagoathletichotel.com/. It's just blocks from Lake Michigan for your morning run.

Museums: All the guidebooks rave over the well-known museums. I'll name three that rarely get mentioned: The superlative Chicago Architecture Center (https://www.architecture.org/), the American Writers Museum (https://americanwritersmuseum.org/) and the Chicago History Museum (https://www.chicagohistory.org/). Of the famous museums, my favorite is the Art Institute of Chicago: https://www.artic.edu/.

Though guidebooks always talk about Millennium Park, here I agree with them: It's worth visiting: https://www.chicago.gov/city/en/depts/dca/supp_info/millennium_park.html.

Culture. I recommend seeing something at the Louis Sullivan-design Auditorium Theater from the 1880s (https://auditoriumtheatre.org/), the bracingly modern Harris Theater for Music and Dance from 2006 (https://www.harristheaterchicago.org/), the Studebaker Theater from the 1890s (https://www.fineartsbuilding.com/studebaker/) or any of those in guidebooks. Also good are the Oriental Theater -- shamefully renamed the Nederlander Theater a couple years ago -- the Chicago Theater or the Cadillac Palace Theater.

Dramatic theater. I recommend the Steppenwolf Theater (https://www.steppenwolf.org/) or Chicago Shakespeare Theater (https://www.chicagoshakes.com/). Chicago Shakespeare is on Navy Pier (https://navypier.org/), which is worth visiting itself.

The Lincoln Park Green City Market is great: https://www.greencitymarket.org/market/details/lincoln

I recommend the Jazz Showcase (https://www.jazzshowcase.com/), which was founded in 1947.

Second City- it is located in Old Town. Check their schedule for shows, times. So many entertainers got their start here.

If you go to the Art Institute (which you absolutely should), don’t miss the often overlooked Thorne Rooms in the lower level. Imagine doll houses on steroids, with the goal of recreating various historical periods.