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emilyrose's avatar

Cool things to do in Chicago?

Asked by emilyrose (2272points) May 8th, 2008

I have never really been before. Other than eating pizza, what should I do? I’ll probably have access to a bike. I don’t necessarily care for touristy stuff, and I tend to get bored in museums if I stay too long. If you have ever lived in Chicago, what are the interesting things I should do while I’m there? I’ll be there for work but will have 2 extra days for free time. What are some cool bike rides to do? Shorter rides, 10–20 miles….

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14 Answers

steelmarket's avatar

Take the touristy ride to the top of one of the skyscrapers (on a clear day!). It is worth it. You can sit in front of one of the floor-to-ceiling windows and see for miles out over the city and the lake. Take your time up there, get to know the city.

robhaya's avatar

I would recommend you go for a bike ride along the lake front along Lake Michigan, you’ll get some of the best skyline views of the city at North Avenue Beach.

Another thing to do is visit Millennium Park, its quite an amazing space and great place to ride your bike too.

I would visit Lincoln Park and do some shopping at the boutiques on Armitage, or any of the other stores on Halstead , between Webster and Armitage. There’s also a lot of good restaurants around that area too.

Good Luck!

chaosrob's avatar

Go see the Bean in Millenium Park. Stop in and have lunch at Geno’s East. Do the water taxi from the Clinton Ave. dock. Go see the Apple store at Michigan and Huron. Check out the Tribune building. Hit Second City for a matinee. Do the CBOT tour. Hit the Billy Goat for a beer. Check out the Museum of Science and Industry, or the Shedd Aquarium. Cubs game. Park at Bryn Mawr and walk up the lakefront (bring a coat). Visit Niketown. Go see “Nighthawks” at the Art Institute. Have a martini at the Hancock viewing deck. Go to the top of the Sears Tower. See the Museum of Modern Art on Chicago Ave, a block east of Michigan Ave.

Have fun!

ljs22's avatar

Chicago has a lot of notable architecture. If you’re interested, check out for their walking and/or boat tours.

Les's avatar

@chaosrob: Wow, that’s a busy day!

buster's avatar

i would go to fenway stadium when the cardinals played the cubs and watch Pujols knock one over the green monster.

emilyrose's avatar

fenway???? isnt that boston?

Sloane2024's avatar

There’s a really amazing Polo Ralph Lauren restaurant that is really reasonabley priced for lunch. I haven’t quite figured out how to add a link to my answers yet, but if you visit ralph lauren’s’s website there is a heading on the sidebar that allows you to view the menu. I hope you have an amazing trip! :)

spywacko's avatar

The week of the 17th and 18th has a bunch of city tours going on. Some of them sound really cool.

marinelife's avatar

I hear you on the museum thing—the brain can hit overload after awhile, but there are such great ones in Chicago, especially the Museum of Science & Industry. Since you’re going to ride it off, don’t forget some of that great Chicago cuisine like deep dish pizza and great steaks. Oh yes, and then there is the blues. (You probably won’t be biking after dark.) You won’t fit it all in in two days—this is one of the world’s great cities—but you can sure have fun trying! Wish I could go too.

jasonjackson's avatar

chaosrob hit some really good ones, especially the modern art museum. I used to take the water taxi across town sometimes; while it’s nothing special really, it’s fun if you’ve never done it before.

One place I think is fun for tourists that he didn’t mention is Jilly’s.. it’s kind of a Chicago institution.

Some additional suggestions:

1. Have drinks or dinner at the Signature Room on the 95th floor of the Hancock building – amazing view. (chaosrob referred to the Hancock viewing deck, which is one floor up; I prefer the bar itself though.)

2. Walk or bike around the Wicker Park area and check out the shops & bars.

3. The Matchbox is a tiny little bar that it can be fun to cram into. It really is tiny, and therefore.. intimate. :)

4. If you’re staying in a downtown hotel, ask your concierge for nightlife suggestions; if he’s any good, he’ll be able to point you to places downtown that will match your interests. Downtown Chicago has a ridiculous number of restaurants & clubs, from moody piano bars to ultra-hip dance clubs, and everything in between.

If you get steered to Division street, just know that the drinking is heavy & a bit wild in that area; maybe that’s what you want, or maybe not. :)

emilyrose's avatar

thanks, everyone! I’m really excited to check it out. Luckily I’ll be staying with locals which will also help. I am very excited for pizza as well!

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