Oh so you only have 48 hours in Chi-town? Well don’t make my mistake – extend that! I’ve consistently heard people say that Chicago is their favorite American city and yeah I think I kind of got a feel on that. The food is good, the skyline is beautiful, and there’s the architecture. But if you only got a weekend, don’t fret, here are the most common Chicago things to do.

It was February. And there’s not a flake of snow on ground. I immediately expel a sigh of relief when I realize this but then my fingers started to complain as I try to type on my fone to signal my sister. She knows the windy city so well that in 48 hours it ended being my kind of town.


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Things to do in Chicago this weekend

1| Millenium Park

Time spent: 45 minutes – 1 hour (no skating)

The Cloud Gate or The Bean is so cool. Well it’s odd really and I don’t get it but it looks so fitting there surrounded by all the pretty Chicago skyscrapers. And then there’s an ice rink that if I only knew how to skate, I’d definitely be skating and put on a show like that dude doing perfect lutz. Skating is FREE but you may have to rent gear.

Tip: There are FREE skating lessons which happens an hour before the rink opens.


2| Chicago Bulls

Time spent: ~2.5 hours

Maybe they’ve had better seasons than now but it’s always nice to watch a Bulls game. Go online and check out their schedule to see if they’ll be playing in United Center.

Tip: Do try the Chicago-style hot dog here because Chicagoans are passionate about their hot dogs and you’ll wanna know why.


3| Willis Tower

Time spent: 1 hour

What’s Willis Tower? Previously called Sears Tower, this building used to be the tallest building in the world. The viewing deck is on the 103rd floor which features a glass platform for those ledge selfies.

Tip: Go early to avoid lines.


4| Field Museum

Time spent: ~2 hours (possibly more for museum lovers)

Field museum is pretty much like most museums I guess but what attracted me to it is Sue. Sue is a T. Rex. The largest specimen ever found according to the museum.

Tip: Watch out for free admission days.


5| Eataly

Time spent: ~2 hours

Eataly is like a market of everything Italian. Food, beverage, bakery, etc. Btw, take note that Al dente pasta is actually a lot firmer than we think. There may still be some white in the middle.

Tip: Since the place is so overwhelmingly big and busy there is the possibility of too much in a day. My suggestion read up for a game plan – here’s a good one from Serious Eats!


6| Navy Pier

Time spent: 1 – 1.5 hours

The navy pier is a wonderful place to watch the Chicago skyline. Time that around sunset and you’ll get dramatic colors. But aside from that there are restaurants, arcades, and shops for souvenir hunting.

Tip: Ever heard of Garrett’s popcorn, there’s a store here so get one cause it’s good.


7| Chicago-style Pizza

Time spent: ~1.5 hours

Deep dish pizza was born in Chicago. A thick and overly filled style of pizza that will surely bloat the tummy. This one below is Gino’s East, one of the populars which also got me to thinking about getting a pizza while writing this.

Tip: As it turns out, it’s big on the tourists so prepare to lineup because there are no reservations.


8| Second City

Time spent: ~2.5 – 3 hours

Another big in Chicago is improv comedy. If you like to laugh and surely you will, get to a show. Second City made the likes of Tina Fey, Steve Carell, etc. Now you must know comedy can be cultural or regional. I liked the show but there were times I was clueless. But my brother-in-law said it was really funny for his local humor.

Tip: Picture taking is not allowed during the show so put away the camera and have a good laugh instead. The pictures below were taken before the show started.