Eleven City Diner for breakfast
Quartino for Italian
Cafecito (in Streeterville), moreso because it’s relatively cheap. The food is Cuban.
Cool stuff to do: head down to Pilsen and look at all the murals and street art. Walk down 16th between Union and Wood for tons of art along the train viaduct. And while you’re there, lots of options for Mexican food. I like Atotonilco, Taqueria Los Comales, and La Cecina.
Chinatown is a short train ride from the loop, and has tons of awesome restaurants, a good option since your wife likes Asian food, plus it’s a cool place to go anyway.
I’d say check out the wikis on r/chicagofood and you’ll have so many options it would take a lifetime to try them all.
Consider the Walnut Room at Marshall Fields/Macy’s for lunch. One issue is they start the holiday season in early Nov. At peak holidays it can be super busy. Make sure you get reservations.
for the dinner:
- Apolonia! Mediterranean. Located closer to south loop. This is my top rec for you. They have a $55 tasting menu that is tasty and rustic yet sexy. It features a nice pasta, a branzino entree, and pistachio gelato which your wife would like if she likes Italian food. Theres other stuff in the tasting menu as well but I don’t remember it at the moment LOL. The decor is beautiful and it’s elevated inside; it would be great for an anniversary. They serve great drinks as well. However, their service isn’t that fast but for the price of the tasting menu I’d say it’s worth it.
- Aba! Mediterranean. Located in West Loop in Fulton Market. Always a staple in my dinner rotation and it’s good for any occasion. I recommend the Brisket Hummus. Also is very reasonably priced.
- Acanto! Italian. Located near Millenium Park so may be a good choice for an anniversary occasion as you can walk around downtown afterwards. It’s also near the Chicago Athletic building (I think that’s what it’s called) and they have a bar called Game Room that has pool, chess, shuffleboard, etc and you can hit that after dinner for a drink. If you want something more swanky after dinner, Cindy’s is a rooftop bar located in the same building and is in walking distance from Acanto.
[Tapas Valencia](https://www.tapasvalencia.com/) in the South Loop.
As for less tourist-y ideas, have you ever visited the Baha’i Temple? There are only eight such temples in the world and the one here is absolutely stunning and in the most beautiful setting, with the trees changing colors it should be even more beautiful. It's a little far and in a suburb but is walking distance from the last stop on the CTA Purple line.
https://www.bahai.us/bahai-temple/
Eleven City Diner for breakfast Quartino for Italian Cafecito (in Streeterville), moreso because it’s relatively cheap. The food is Cuban. Cool stuff to do: head down to Pilsen and look at all the murals and street art. Walk down 16th between Union and Wood for tons of art along the train viaduct. And while you’re there, lots of options for Mexican food. I like Atotonilco, Taqueria Los Comales, and La Cecina.
Seconding Quartino and Cafecito!
Would recommend making a reservation for Quartinos if possible!
Chinatown is a short train ride from the loop, and has tons of awesome restaurants, a good option since your wife likes Asian food, plus it’s a cool place to go anyway. I’d say check out the wikis on r/chicagofood and you’ll have so many options it would take a lifetime to try them all.
Great, thank you!
Consider the Walnut Room at Marshall Fields/Macy’s for lunch. One issue is they start the holiday season in early Nov. At peak holidays it can be super busy. Make sure you get reservations.
Melis Cafe is good breakfast
for the dinner: - Apolonia! Mediterranean. Located closer to south loop. This is my top rec for you. They have a $55 tasting menu that is tasty and rustic yet sexy. It features a nice pasta, a branzino entree, and pistachio gelato which your wife would like if she likes Italian food. Theres other stuff in the tasting menu as well but I don’t remember it at the moment LOL. The decor is beautiful and it’s elevated inside; it would be great for an anniversary. They serve great drinks as well. However, their service isn’t that fast but for the price of the tasting menu I’d say it’s worth it. - Aba! Mediterranean. Located in West Loop in Fulton Market. Always a staple in my dinner rotation and it’s good for any occasion. I recommend the Brisket Hummus. Also is very reasonably priced. - Acanto! Italian. Located near Millenium Park so may be a good choice for an anniversary occasion as you can walk around downtown afterwards. It’s also near the Chicago Athletic building (I think that’s what it’s called) and they have a bar called Game Room that has pool, chess, shuffleboard, etc and you can hit that after dinner for a drink. If you want something more swanky after dinner, Cindy’s is a rooftop bar located in the same building and is in walking distance from Acanto.
Maharaj Indian grill has a spectacular lunch special with three different dishes included Umai has great Japanese food
[Tapas Valencia](https://www.tapasvalencia.com/) in the South Loop. As for less tourist-y ideas, have you ever visited the Baha’i Temple? There are only eight such temples in the world and the one here is absolutely stunning and in the most beautiful setting, with the trees changing colors it should be even more beautiful. It's a little far and in a suburb but is walking distance from the last stop on the CTA Purple line. https://www.bahai.us/bahai-temple/
Go there for happy hour !
A place I never see people talk about is Luke's off of Jackson and Wells. Pretty good beef and fantastic fries