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kevbo's avatar

Suggestions for a night and a day in Chicago?

Asked by kevbo (25603points) August 26th, 2010

I’ll be in Chicago with a college buddy for a night (say 8 p.m.) and part of the next day (until 2 p.m. when I’ll have to leave for the airport) from Sept 25–26. I’ll be staying downtown off Michigan Ave and Grand Ave and will have a car.

I don’t really know anything about Chicago, and I don’t really have a natural affinity for the city (like I don’t dream of traveling to Chicago someday to do all the cool stuff there). So I need some help.

What are some cool things to do that will fit the time?

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16 Answers

Hawaii_Jake's avatar

If you enjoy theater, the Chicago Shakespeare Theater is one of the best in the world. They’re right on Navy Pier. The Steppenwolf Theatre Co. is also one of the best.

truecomedian's avatar

Go for a cruise along the lake, Lake Shore Drive. Maybe go north and hit a Sushi bar. Check out Ricobene’s and get a breaded steak sandwich on garlic bread with sweet peppers. Check out China town, Seven Treasures is known for its pan fried noodles and has really good hot sauce. I used to manage a restaurant in Chi Town but that was years ago. Maybe the movie theater that serves drinks is more your style. There is really good food it in Chicago. Be careful where you drive there are some rough spots like in any city. Probably going to be hot, so there will be a lot of people chilling at the lake. Explore, keep in mind how the city changes from block to block somewhat. Good Greek food.

Cruiser's avatar

Got to go to Sears Tower and do the brand new glass floor balcony a zillion feet up over the city and test your ability to hold your lunch it will be an hour of your life you will never forget!!! I would definitely hit the House of Blues and see a show there. The Art Institute, Field Museum, Museum of Science and Industry are world renowned if you are into the arts they are all must sees. I would hit Michigan Ave or Oak street beach and you will be right by Navy Pier walking distance and there is a ton of real touristy stuff to do there…gotta ride the ferris wheel it it ginormous!!. Shit there is more to do here than the rest of the country combined….Lived here my whole life and PM me your likes and I will tell you where to go!

jazmina88's avatar

The Art Institute and the Aquarium, there are beluga whales there.

Aethelwine's avatar

Chicago Horror Film Festival

Chicago Gourmet Food Fest ouch, just looked at the price for that :/

4th Annual Hyde Park Jazz Festival free

damn. If Jon and I weren’t moving that weekend, we’d meet up with you for drinks!

jaytkay's avatar

Welcome! I always tell people September is the best bet for perfect weather in Chicago, I hope that weekend proves it!

A few ideas:

Go the beach. From your hotel walk or cab ¾ mile north on Mich Ave to Oak Street. At the Northeast corner, you’ll find a walkway taking you under Lake Shore Drive to Oak Street Beach.

If Indiana Jones had a museum, it would be the Oriental Institute at the University of Chicago. It’s about a 20minute drive from your hotel. Built in the days when wealthy Americans could visit Iran & Egypt and parts in between and steal everything they could carry.

While you’re in Hyde Park catch the carillon concert on the same block at Rockefeller Chapel

The big institutions will not disappoint, these are all a short cab ride from N Mich Ave:
Art Institute of Chicago
Field Museum
Shedd Aquarium
Adler Planetarium
Lincoln Park Zoo

If you have more specific needs/wants (food, movies, music, time, place budget,etc) let us know and the ideas will flow!

Qingu's avatar

Hopleaf is the best bar in town, in my humble opinion. Humble indeed because I don’t even like to drink. But it is said their beer is amazing. Their food is really good, too. Belgian-style frites.

jaytkay's avatar


Friday the 25th here is a good concert in my neighborhood (for my taste, again I am just throwing out ideas.)

Kinobe & Soul Beat Africa and Meklit Hadero
Kinobe Herbert is a multi-instrumentalist and singer-songwriter from Uganda, who leads his listeners into the soul of African music with traditional instruments, songs, and stories from his homeland. His shows feature the kora, kalimba, tama, and an array of traditional percussive instruments, all crafted and brought to life by his skilled hands.

If Joni Mitchell were East African and met Nina Simone for tea in San Francisco’s Mission District, she might end up sounding like Meklit Hadero.

This would be an easy trip from N Michigan Ave by El train.

Or Second City is fun, they have two 8PM shows, the Main stage or the cheaper ETC (which is a fantastic deal, either show will kill you). You can see the future stars of comedy today!

For discount theatre tickets see

Feel free to send me comments with questions about getting around or whatever.

Mostly I would recommend NOT spending Friday evening near the hotel, the neighborhoods away from downtown are more fun, easy to reach, safe and cheap.

lillycoyote's avatar

Chicago is a great city for architecture if that’s something your interested in. Chicago is a city I’ve been to 4 times and still spent probably less than 48 hours there total. There was period when I just stopped there on the way to somewhere else. I took a cross country train trip and had a maybe 6 hours layover there and I called a friend of mine and asked her what to do and she put together an architectural tour of the city, near the train station, in just a few minutes. Well, anyway, I enjoyed it a lot and if you have a car/transportation and can get to the Frank Lloyd Wright houses, even better. Here’s a link if it’s something you’re interested in. Also, Chicago did, and hopefully still, does, have some great jazz clubs for something to do at night, if you’re into that. Someone who lives there, or has been there more recently, could give you more insight into that than I can.

lillycoyote's avatar

Here’s another link about Chicago archictecture, pretty basic, I’m no expert.

mowens's avatar

No one mentioned the Signature Room? IT IS A MUST. Go there for lunch, it isn’t priced to high for lunch. Dinner, is expensive.

Go, and love me forever. It is at the top of the John Hancock Building.

kevbo's avatar

Hi all,

Just wanted to say thanks for your many great suggestions. I ended up taking the Shore Line Architectural Tour (on the river), walking some of Navy Pier and the Magnificent Mile, going to the Signature Room (but wasn’t hungry enough for a $45 brunch buffet), and wandering through Millenium Park. Downtown is really lovely and omg so are the women—holy cow. It was a great time. I’m sure I’ll be back. Thanks again.

lillycoyote's avatar

@kevbo So glad to hear that you had a good time and got to see some of the great architectural sights that Chicago has to offer. I will have to check into the Shore Line Architectural Tour if I ever get back there. Boats and buildings; that’s gotta be good!

mowens's avatar

@kevbo My lunch was 8 dollars there last month? What the hell are you ordering?

kevbo's avatar

The $45 buffet was the only item on the menu. It was Sunday brunch.

Aethelwine's avatar

So happy you had a great time. Illinois is a wonderful state. :)

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