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🔖 travel   recommendations

Chicago Recommendations

Chicago is known as the windy city, not because of its wind, but because of its terrible politics. That said, if you visit between late September to April, bring winter wear.

Also, some of my information may be out of date. I lived in Chicago for the summer of 2014, and went back for a week in 2015 and 2017. I would love to make plans to come back.

Where to Stay


Chicago is super walking and transit friendly. Since the city sold their parking meters to a bank, it’s super expensive to park around the loop (i.e. the downtown and Millennium Park). I recommend CTA’s L Train to get most anywhere you need to go and walk from there. If you stay in any of the above, there’s a huge chance the L will run near it.

Cultural and Seasonal

I already mentioned Pride month. During the summer, you’ll find block parties as well.

Music is huge in Chicago, whether that’s music festivals like Lolapallooza, Riot Fest, Pitchfork, or checking out the House of Blues, and far too many music venues to list.

There are so many cultural enclaves when you explore Chicago.

If you’re a comedy fan, there are great live shows from Second City. There are many prominent names who’s come out of here, including Stephen Colbert, Steve Carell, Tina Fey, and Amy Poehler.

If you want theater, they have their broadway and off-broadway shows as well.

Year Round Places to See

Foodies Beware

Chicago is a food hub for some serious high-end restaurants, as well as some great local staples. Since you have to reserve far in advance for some of these, I’ll leave the high end ones at the front.

For more common day food, Chicago has a lot to offer.

If you’re looking for that Chicago deep dish, the easiest place to find it is in a chain of restaurants called Lou Malnati’s. Order ahead, as it may take up to 30 minutes for them to bake it. There’s of course a ton of other options. I know on my list to check out is Burt’s Place where they serve it to you in the pan.

The other prominent Chicago-esque food is the Chicago Dog. I personally don’t care for it as much as others do, but if you like this pickle hot dog contraption, check out Fastso’s Last Stand. Also, other places.


Written by Jeremy Wong and published on , and last updated on .