Chicago
The STANDARD H Travel pages are our version of city guides presented by our founder, Wesley Smith. These are places he's traveled, enjoyed, and recommends, so they're all vetted and what we refer to as STANDARD H verified. These lists will evolve, so check back often and travel safe!
The Girl and the Goat
809 W Randolph St, Chicago, IL 60607
One of the best meals I've had in recent memory. I was just there (August 2024). You will definitely need a reservation, and as far as the menu goes, it's full of items you may be very unsure of, while they will all surprise the hell out of you in the best way possible. The combinations of ingredients and flavors is almost unlike anywhere I've ever been before. HIGHLY recommend this place.
Au Cheval
800 W Randolph St, Chicago, IL 60607
If you've read most of the Travel section on this website, you'll know I love two things: pizza and hamburgers. Au Cheval is arguably a life-changing hamburger. They don't take reservations, so you will absolutely want to get there early, and then grab a drink two doors down at Nisos Prime.
The Purple Pig Restaurant
444 Michigan Ave, Chicago, IL 60611
This Mediterranean spot is very much a wine bar feel with quite an extensive menu. Great spot for appetizers or a charcuterie board, or if you're like my wife and me, enjoy a 2.5 hour dinner with every course known to man! Jokes aside, this place was delicious, and though the menu is indeed large, it only means you'll be guaranteed to find something you like. The service was great and the wine list was very good, as well. I would say this is a great date spot, or a great place for parties up to 4 people. It's an energetic environment, so parties much larger will just result in you not hearing the other end of the table anyway.
Gather
4539 N Lincoln Ave, Chicago, IL 60625
When I was in Chicago for Windup Watch Fair 2022, I went to Gather with 5 friends and had such a great time. The service was top notch and so was the food. I ordered the Chicken - sounds boring but they're kind of "famous" for it actually and it did not disappoint. It was incredibly tender and really delicious. Gather is the kind of place, however, where you can simply close your eye, point to the menu, and whatever you land on, it's bound to be tasty.
LH rooftop at LondonHouse
85 E Wacker Dr 22nd Floor, Chicago, IL 60601
My wife and I grabbed cocktails here with a friend. The drinks were fairly standard, nothing of note, however, the views are unparalleled and the real reason to go. Great for a date or a group of friends/business associates.
Architecture Boat Tour
This is listed first for a reason: it's unlike anything you'll experience in any other city. If you're into architecture, this should be the first thing you book before any dinner reservation. And if you're not into architecture, trust me, it's great. At the very least, it's a great way to see the city from a perspective you otherwise can't experience.
Cubs Baseball/Wrigley Field
1060 W Addison St, Chicago, IL 60613
I wouldn't normally showcase a team, let alone a stadium, but Wrigley is different. If you are planning to go to Chicago, I've always said October is the best. You can wear a jacket and you may even encounter a 70-degree day. The leaves along Michigan Avenue are changing and it's just beautiful. However, if you like baseball, or even if you just like history, visit Chicago in May and take in a game at Wrigley. Built in 1914, it's only two years newer than the oldest ballpark in the majors (Fenway Park in Boston - 1912) Wrigley was the last to receive lights in in order to play night games, which didn't happen until 1988! The afternoon games are really traditional, especially if you're of a certain age and recall Harry Caray announcing the games. Ideally, go to a Friday afternoon game. Business people from all of the city skip out of work early, many just loosening their ties to drink beer and scarf down a hotdog or two. To me, Chicago is perhaps the best sports city in the nation, though the people of St. Louis will have an issue with this statement.