3 days, 2 nights in Chicago

Not sure how old your daughter is, but, the Lincoln Park Zoo is free. And next to that there is a nature boardwalk on one side and a plant conservatory on the other. There is a beautiful view of the city and a pond in front of the north pond restaurant (expensive). These things are all next to each other in Lincoln Park.  

I would definitely take an architectural boat tour beginning at the river. You can enter near the The Wrigley Building. You can also grab some food around the river too. But if you get the tour in and/or walk around there, I'd skip the food down there and go to some of the other suggestions. If you want to see Wrigley Field it is in Lakeview.  

For restaurants, My friend and I both love True Food Kitchen, sweetgreen is across the street from there is fast casual, but it's excellent! Lou Malnati's Pizzeria is my favorite pizza. Friends Sushiis great. Carmine's is great. Rosebud Prime is great. Hugo's Frog Bar & Fish House and Gibsons Bar & Steakhouse are great. Morton's The Steakhouse is great. One of my all time favorite places is Le Colonial Chicago. My other favorite is Doc B's Fresh Kitchen - Chicago River North! My third favorite is Bandera. Another favorite of mine is Roy's. And lastly, anything on W Randolph StHalsted & Taylorin the west loop (basically restaurant row) you can't go wrong with. Au Cheval is a popular burger place. My favorite burger place is down the street from there. It's called Grange Hall Burger Bar. All the Gpat restaurants are there too. Girl & the Goat is the original Top Chef place there. And one of her other restaurants is across the street from there. Others I like are Summer House Santa Monica, LYFE Kitchen, The Little Beet Table(all gluten free but amazing), Lokal (Bucktown), Beatrix, Uncommon Ground, (a farm to table restaurant by Wrigley (via Kennedy) 

There are excellent brunch places. Bongo Room, Yolk, Beatrix, Kanela Breakfast Club Kingsbury Street Cafe, Orange Restaurant Chicago, Lincoln Park.

For hotel location I think River North is centrally located. There are so many options. Godfrey Hotel, The Aloft Loft, Dana Hotel and Spa are fun options. The The Langham, Chicago hotels are nice and great locations but not sure about pricing. I would definitely encourage the boutique hotels. They are the most interesting. The The Ivy Boutique Hotel, the James Hotel, and the Hotel Lincolnare both nice. I live near Hotel Lincoln in lincoln Park (a few blocks from the zoo and across from a beautiful park, the largest farmers market on Saturday, and the Nature boardwalk and plant conservatory.  

There's a great music (City Winery at the Chicago Riverwalk Park West, Space), theatre (Broadway shows and non-musical shows like the Steppenwolf Theatre and a few Shakespeare options), dance, and museum scene. Shedd Aquarium, The Art Institute of Chicago(I love the modern wing), Museum of Contemporary Art

Lots to choose from. Good luck and enjoy! I'm happy to answer any questions directly if you want. Not sure if that's an option on this app.

If I had to stay in Chicago, I would stay in River North, as close to N Michigan Ave and the Chicago River as possible or on the south side of the Chicago River.  You have lots and lots of hotel options.  Virgin Hotels Chicago is a good choice, I was really impressed when I visited during Open House weekend.  I'd also have a look at the Chicago Athletic Association on S. Michigan Avenue which was turned into a boutique hotel.

For art, you'll want to check out the The Art Institute of Chicago of course, you can do a walk to see some of the public sculpture such as the Picasso, the Miro, the Calder and the Chagall mosaic, all within a short walk of each other.

For a boat tour, I'd go on the Chicago Architecture Foundation's tour if you are an architecture buff, if not, Wendella or Shoreline are also fine.

I don't eat downtown all that often anymore, when I do I like to go to Little Goat Diner in the West Loop, Havana Grill in River North for Cuban, Lou Malnati's Pizzeria for deep dish pizza, Giordano's Pizza for stuffed pizza.  For a splurge, I go Joe's Seafood, Prime Steak & Stone Crab, reservations are absolutely essential.  For steak I like Wildfire and Morton's The Steakhouse.  For casual Mexican you can go to XOCO.

Do not plan on eating at Navy Pier, we've had a few meals there lately because we had tickets to Chicago Shakespeare and all of them were overpriced and not all that good.  But if you want to see a good show, the productions at that theater are usually top notch.

I love the Gold Coast area. There are several great hotels in that neighborhood, but River North is a nice area too. If the weather is nice you can walk all over the city. Navy Pier is nice, OakSt beach, any of the museums, the Shedd Aquarium, although in summer lines tend to be long. Lincoln Park area is very nice too.

I love the Gold Coast area. There are several great hotels in that neighborhood, but River North is a nice area too. If the weather is nice you can walk all over the city. Navy Pier is nice, Oak Street Beach, any of the museums, the Shedd Aquarium, although in summer lines tend to be long. Lincoln Parkarea is very nice too. If youre staying in the Gold Coast, Pizano's Pizza and Lou Malnati's Pizzeria have great pizza. Del Frisco's Double Eagle Steakhouseis a good steak house, Tavern on Rush and Carmine's are nice not too expensive restaurants. Of course Gibsons Bar & Steakhouse and Hugo's Frog Bar & Fish Houseare the big tourist draws.

There is the Chicago Architecture Foundation River Cruise and also you might consider the Oak Park (Illinois) tour of Frank Lloyd Wright's house and of the houses he designed in that area.  I ate at the Billy Goat Tavern with a work colleague but she was disappointed that there were no vegetables on the menu. :)

Welcome to Chicago. As for a hotel, I have stayed at the Marriott JW Marriott Chicago. The The Art Institute of Chicago is beautiful. For a boat tour I recommend Wendella Boat Tours along the river or go to Navy Pier and take a Shoreline Cruises. Both are very nice. For more fun, check out the Shedd Aquarium or the museum of natural history As for dining, I recommend Bandera, True Food Kitchen, Rosebud on Rush, Eataly Chicago and Labriola Chicago. Definitely try Giordano's, too. If you like deep dish, check out Gino's East South Loop. Enjoy!

My hotel suggestion would be a boutique hotel like Virgin Hotels Chicago on Dearborn Station Galleria near Lake. Very convenient to everything. What type of restaurants do you like. There are many mid-priced restsurants. I retired a few years ago and actually lead private and public tours of Chicago and its neighborhoods. If you are interested, let me know and I can provide more details. Rich