A Snob’s Guide to Chicago
I started visiting Chicago regularly after college, when my closest friends moved there. We went to the old Bistro 110 and felt very proud when we graduated to drinks at the Violet Hour and the Aviary, and then dinner at the Publican and Girl & the Goat (still favorites). There are things on this list I’ve loved for 30 years. Others became musts more recently. I also get a little help from my highly opinionated friends and family. Let’s call them the HOFs.
1. Check into the recently refreshed and perfectly located Park Hyatt Chicago. Ask for a lakeside room (on an upper floor). The Lake Michigan and Park Suites feel as if you are actually on the water.
2. “Walker Bros. for breakfast!” HOF and Chicago native Brooke Garber Neidich advises. “49ers pancakes, very crispy bacon, fresh-squeezed OJ.”
3. Take an architecture cruise. I like the Chicago Architecture Center River Cruise. I do this every time.
4. Have lunch at RL. Before Polo Bar in New York, before Ralph’s in Paris, there was RL in Chicago. It’s the OG.
5. Check into the Peninsula Chicago. Also right there on the Magnificent Mile. Have afternoon tea in the lobby and dumplings at the Shanghai Terrace. In winter ask about the skating rink!
6. The Langham (and its big, gorgeous rooms) is also a favorite.
7. Walk along Michigan Avenue to the Art Institute. (On the way, take your Kapoor Bean selfie.) The Thorne Miniature Rooms are a must, as is the Seurat that inspired Sondheim and Grant Wood’s American Gothic. The museum website has a great “what to see in an hour” guide.
8. ”The Field Museum of Natural History is also fabulous,” interjects HOF William Li. “The Hall of Jades! Go.”
9. “And the Fairy Castle at the Museum of Science and Industry!” Brooke says.
10. Riverwalk? Yes, says HOF Kate Chappell, news anchor for NBC Chicago. “End with sunset views at Tiny Tapp.”
11. Do the Frank Lloyd Wright Home and Studio tour in Oak Park. Ice cream at Petersen’s (around since 1919) afterward.
12. “Go see Robie House,” says my HOF niece and Chicago undergrad, Cayla, of Wright’s landmark. Reservations required. Afterward “get a Mediterranean omelet cafeteria-style at Valois, and try to sit at President Obama’s table, or have excellent Southern-inspired food at Roux.”
13. See a show at the Goodman Theatre. The hot ticket for 2024 will be Taylor Mac and Rob Ashford’s Midnight in the Garden of Good and Evil (June 25–August 4).
14. And at the Steppenwolf. Laurie Metcalf will star in an as yet untitled show. It doesn’t get more Chicago than that.
15. And anything at the Lyric Opera.
16. “The chorizo-stuffed bacon-wrapped medjool dates at Avec,” I say.
17. “A steak and a martini at Gene & Georgetti!” Brooke says.
18. “The tuna crudo and stracciatella appetizer at Rose Mary,” Cayla says. (I second this, and also a walk around the Fulton Market District.)
19. “The Hong Kong–style roast meats at Sun Wah BBQ,” William says.
20. “The chicken pot pie, truffle bucatini, and the burger at Armitage Ale House,” Cayla says.
21. “Pasta at Monteverde. Any of them,” says basically everyone you will ever talk to.
22. “The thin crust pizza at Nancy’s in West Loop,” Kate says. That’s all I’ll say on the pizza matter.
23. The Kalamata chicken at the Athenian Room. It’s how Chicago theater royalty Carrie Coon and Tracie Letts celebrate their anniversary. (If that doesn’t matter to you, the rest of this list might not either.)
24. Wait in line for the Au Cheval burger. It’s a rite of passage. Same goes for dinner at Alinea. I have never been, and am ashamed.
25. Go to a Garrett Popcorn shop before you leave. Get tubs of the cheddar-and-caramel. Bring me some.
This story appears in the October 2023 issue of Town & Country. SUBSCRIBE NOW
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