jessiejames
Never late in a V8
Last time i was in Chicago, March a few years ago, went horse racing at Hawthorn park in the snow and freezing cold, flew home 2 days later 70 degrees.
A similar story for us, but we eventually made it to NYC this August. At the third attempt after the pandemic ended 2020 and 2021 bookings.
My original plan was NYC and either Boston or DC but, not exchange rate related, the total cost would’ve got out of control. ‘Just’ NYC was a happy compromise.
$1.20 to the £ was the rate we got. A $1.07 tourist rate today, if you shop around.
The US, for several reasons including the exchange rate, has become expensive in general. My parents did many great road trips in the US on the 90’s and early 00’s. They were paying next to nothing for hotels and meals. When we went to Florida 5 years ago, it was different ball game, $100 plus a generous tip for Denny’s type meals for 4.
My advice (which you’re not asking for ) is to tailor it to just NYC and just go. An amazing city, so much to do, we didn’t see it all in 11 days. Grab the cheapest flights and there’s lots of hotel capacity …. cabbies told us the city had never recovered in any shape or form the lockdowns.
There won't be a game on but I would recommend a tour of Wrigley Field. Iconic stadium and some interesting history about the team and city. There is a bar near the stadium called Sluggers which has batting cages upstairs, which is fun.
100% do an architecture tour. They take you on a boat down the river and onto the lake. Lots of great views and the MC tells you lots of great Chicago history.
As others have mentioned, the Skydeck.
The Bean is an iconic landmark but only worth stopping at on your way to/from somewhere.
For food, Little Goat Diner has amazing breakfast/brunch. The sister restaurant Duck Duck Goat is very good for dinner. Italian beef sandwiches are famous in Chicago, with Al's #1 Italian Beef being the best known. Portillo's is also a famous spot for Chicago-style hot dogs. For Pizza, Pequods and Lou Malnati’s are the high profile ones but you would certainly be able to find better once you're there just by asking around. Au Cheval is a super famous burger place but the line is always hours long… BUT they have other locations called “Small Cheval” which is more of a fast food spot and the burgers are still very good.
On food, don't miss the original* Billy Goat Tavern just off (actually under) Michigan Avenue, a subterranean greasy spoon that was the hangout for the journalists at the nearby Tribune and the Sun-Times offices.
If you have only a couple days can stay more centrally, but if longer then Evanston where North Western Uni is, is nice for a slow day. On the lake shore, bit of a slower pace and easily walkable by American Standards. Good excuse for a short, iconic train ride out there too on their equivalent of a tube.
I remember the bean, a pier and canals Centrally, but spent most of my time at the university, eating food and chilling in the suburbs with a friend sorry.
It’s all a bit 25 or 6 to 4