Re: If we make it to Chicago:
ha, well we like steak but probably not doing a steakhouse. I'd say we are pretty varied - do not like very spicy food (do like Mexican food) or weirdly fancy. Outside of that we are pretty open.
There's a ton of places just in the downtown area. Way more than I can even begin to suggest a ton on here, but here's some:
Italian:
Volare, La Madia, Quartino, Nico, La Scarola, JP Graziano (a deli - more of a sandwich place)
Burgers
Rockit, Grange Hall, Au Cheval (rated best burger in America not long ago - no reservations and wait times can be very long. Foie Gras & Eggs there is amazing as well).
American (maybe more of an elevated kind)/Gastropub
Mad Social, Publican, Publican Quality Meats, Oak + Char, Gilt Bar, Bottlefork, Beatrix, The Gage, Sable, Maple & Ash (more steakhouse, new - but not a typical steakhouse at all), Pump Room, River Roast, Farmhouse, Green Street Smoked Meats (BBQ).
Purple Pig and Girl & the Goat are also amongst the top, though PP doesn't take reservations and can have long waits and Girl & the Goat might be hard to get a reservation.
South American (no, it's not all spicy)/Tapas/Other European
Bar Takito, La Sirena Clandestina, Vera, Tanta, Havana, Cafe Iberico, Enolo, La Sardine, Maude's, Carnivale
Asian/Indian
Urban Belly, Boozebox/Sushi Dokku, Sunda, India House, Talay, Jaipur, Ramen Takeya,
I also love Le Colonial which is a little more fine dining,but upstairs is a lounge where you can order anything. You will not feel like you're in the US anymore - it's all 1920s/1930s SE Asian plantation from Vietnam. Kind of an unknown celebrity hang out. You don't need to be super dressed up to go there, but don't show up in your ISU gear or anything. Jeans/sweatshirt is completely fine. Food is great too, though it's more refined Vietnamese food from when France ruled it.
Momotaro too - expensive, but if you're a sushi purist, there's not a lot of better places in the US. They have a downstairs Izakaya too with a little bit of food that's cheaper but the menu isn't huge.
Sweets/Coffee/Tea
Stan's Donuts, BomboBar (attached to Bar Siena), Intelligentsia, 3 Arts Club Cafe (most beautiful cafe I've been to in the US - long waits but..damn), Sawada,
Most of the places I listed are not a jacket/slacks type of place. You can show up to any of these pretty much with jeans/sweatshirt (not like a sports one, but a normal, decent sweatshirt) or jeans/button down. Most places in Chicago are pretty casual like that.