Chicago!

September 3, 2008 11:44 AM

What can I do to make one perfect night in Chicago?

Alright, I've searched through previous posts, but am looking for something very definitive. After my last post, I decided to travel to Chicago! I'll be there by myself from Sept 7th, with my SO joining me on the 9th; we're both flying back to CA on the 10th.

What can we do with that one night together that would be a classic, authentic Chicago experience OR what can we do to make it a really great night in a city we've both never been to?

posted by brynna to travel & transportation (15 comments total)

definitely do a late evening cocktail at the 99th floor (is it still called the Signature Room?) at the Hancock. the view is worth it, and it's way better than paying to go to the observatory. make sure to press yourself against the window in the chicks' bathroom. wow.

others will have better suggestions otherwise.
posted by RedEmma at 12:07 PM on September 3, 2008

I'm a fellow Californian who visits friends in Chicago often. Some quick thoughts...

Food: I've yet to make it here, but local friends have recommended the Signature Room. For deep dish pizza, I'm a fan of Giordano's, but there are plenty of great pizzerias. Also, many sushi places are Bring Your Own Booze. So bring a nice bottle of wine/sake and enjoy!

Art: Millennium Park has some great events, and the concerts on the grass are quite fun.

Classic chicago: Looks like the Cubs are playing away, but you could catch a game on the telly somewhere in Wrigleyville. And don't forget Navy Pier for some touristy shopping and tasty fudge.
posted by smbird at 12:26 PM on September 3, 2008

I have lots of Chicago suggestions, but can you offer a little more information about the types of things you and the SO like? Chicago is such a wonderful and varied city that I'm sure you can come up with something that's both very Chicago and ties in to other things you enjoy.
posted by j-dawg at 12:50 PM on September 3, 2008

Sure, Millennium Park, The Bean, the face fountains, Buckingham fountain, then over to Navy Pier and a ride on the Ferris wheel, take a Wendella boat tour of the river and or lakefront (You can catch them around the river at Michigan avenue and the river).

You could catch a Sox game, just as easily accessible from downtown via the redline as those boogers on the north side.

Also, I always recommend people catch Too Much Light Makes The Baby Go Blind, its 30 plays in 60 minutes, but you'd have to do it Sunday night, and the show is at 7pm. Get dinner at Reza's just a block or so away, order the beef and chicken shishkabob combo, and have dolmeh as an appetizer. yum.
posted by Reverend John at 1:19 PM on September 3, 2008

As far as things we like - we definitely like eating out, so are looking for a GREAT place that's modern and delicious for that night. after that, we'd probably love to see a comedy show, concert, etc. we're so excited!! :)
posted by brynna at 1:25 PM on September 3, 2008

Seconding Reza's! Fantastic, always stop in whenever I'm anywhere near Chicago. Also try the eggplant steak as an appetizer. I'd go there just for the default soup you get with every meal....
posted by dragstroke at 1:26 PM on September 3, 2008

oh I want to piggyback on this post! My girlfriend and I are going to be in Chicago for a weekend to play an away game (roller derby) and have extended our stay a day so we can experience the city. It will be her birthday so I want to make it really special. One catch: I'm a city mouse but she's a country mouse. Our one day and night for adventure will be Sunday, September 21.
posted by palegirl at 1:29 PM on September 3, 2008

check out the Neo-futurists play "Too Much Light for the Baby"...it's improv comedy, with 30 sketches, and very funny.

or go to Yelp.com...and type in Chicago "comedy", to see which activities are most popular. For food ideas, go to chowhound.com.
posted by yoyobates at 3:25 PM on September 3, 2008

Thirding Reza's. If you like Broadway-type stuff, go see Wicked at the Oriental Theater.
posted by Stylus Happenstance at 3:27 PM on September 3, 2008

Don't laugh, but the Architecture Foundation gives incredibly great tours. Millenium park is really amazing. I would say make a visit to the art museum. For some reason I love being there at closing time.

There are a couple of classic restaurants on the loop. There are better restaurants, but these are sentimental favorites. One is the Berghoff, which just radiates old Chicago. If you want something a little more swank, you could try ">Shaw's Crab House, mostly for the fantastically well preserved interior.

I no longer know the great blues bars, but I do like going to the top of the Hancock building for a drink at night. Of course, many people consider it to be a tourist trap, which it is, but it's a lot of fun.
posted by gesamtkunstwerk at 4:52 PM on September 3, 2008

My significant other and I (who are pretty big foodies and cocktail fans) recently had a fabulous night in Chicago where we visited the Violet Hour for pre-dinner cocktails and then did the tour at Alinea (all 24 courses).

If you're at all interested in playing with your food or eating at a restaurant that's pushing the boundaries of food, go to Alinea. It's an experience that's enhanced by the story of the insanely talented and young chef who left a sous chef position at French Laundry to strike it out on his own, opened a critically-acclaimed restaurant, and then found himself diagnosed with Stage IV tongue cancer. (There is no Stage V).

Call Alinea as soon as possible. I can't recommend the experience enough.
posted by kathryn at 6:36 PM on September 3, 2008

First of all, I strongly suggest checking out the Chicago Reader online (www.chicagoreader.com) before your trip. It's the city's alternative newspaper and carries very thorough and up-to-date listings, reviews and descriptions of all the of cultural activities, restaurants, attractions, museums, sports events, etc. Use this to narrow down your options, because there are a lot. Printed copies are readily available at hotels, streetcorners, restaurants, etc.

Comedy: Definitely try to get tickets to Second City (it's where many of the most famous of the SNL casts got their start). It's always a great show.

Restaurants: Chicago is a world-class restaurant town. Your won't find the best of them in the Loop however, which mostly caters to office worker lunches. The North Michigan Ave. area, and the north and near west neighborhoods, are chock-full of great places. Ethnic, cutting-edge molecular gastronomy, wood-fired pizza, fine dining, whatever. I've eaten at NoMI a few times, and I recommend it as fine dining experience for the food alone. But what's unique about it is the spectacular view (see nomirestaurant.com for a better idea). With higher-end places like this, though, try to make reservations ahead of time.

Neighborhoods: North Michigan Avenue and the Loop are best known to outsiders, but you won't get a true sense of Chicago without exploring the neighborhoods (Chicago is called "The City of Neighborhoods"). Get on the bus that goes up and down Clark Street (or Lincoln Ave.), then hop on and off whenever you see something you want to investigate further. Or just walk up Clark Street (or Lincoln) and take the bus back. There's gobs of cool shops, restaurants, etc., for miles. Or take the El in a direction, get off at a stop and look around, then get back on.

Transportation: As soon as you arrive, get a "Chicago City Finder" map. It's a laminated tri-fold map that's very clear and shows you all the bus and train routes. Definitely ride the El, especially the part that "loops" the Loop. Public transit is safe, easy and very efficient, plus you can save all that cab money for your blow-out restaurant meal.

Tours: The boat architectural tour is GREAT. Chicago is THE premier US city for architecture, and this tour will really make you feel you've experienced Chicago buildings and history. It's not "dry" at all, the guides are great storytellers, and the view as the boat winds down the river with amazing skyscrapers on each side is magnificent.

Navy Pier: I'd skip it unless you're nuts about Ferris Wheels. It's full of chintzy, overpriced tourist shops that specialize in t-shirts and novelties. It also takes forever to get there, since it's not on a direct transport line, and once you do there's not much to see - it's like a bad mall, albeit a mall with a view.

Instead (if you want a picturesque walk), there's a lovely path along the lakefront that goes on for miles.

Museums: the Museum Campus is home to the Field Museum, Shedd Aquarium, Adler Planetarium and Soldier Field (and accessible by bus). And, of course the Art Institute on Michigan Avenue, home to a superb collection of Impressionist paintings.

Music: for a true Chicago experience, check out the blues clubs. My personal favorite is Kingston Mines. For great jazz in a space that hasn't changed since the 1930's, don't miss the Green Mill. It used to be owned by Al Capone, and the space is like a time capsule. Just get there early if you want a seat.

To second previous suggestions, I also strongly recommend Millennium Park, the"Too Much Light" play and a cocktail in the Signature Room in the Hancock Tower as worthwhile and unique Chicago attractions.

Have a lovely time, and let us know how your trip went!
posted by lipstick bookworm at 7:10 PM on September 3, 2008 [2 favorites]

Wow, thank you everyone, so much!

I was actually really interested in Alinea for the solo portion of my trip, but they're closed all the days we'll be there! I've booked an Architecture Foundation River Tour, thanks for that suggestion.

I'm really excited, thanks so much for the great answers!
posted by brynna at 9:28 PM on September 3, 2008

Don't miss "Too Much Light Makes the Baby Go Blind" after your boat tour.. it starts late at night and is AAAAWESOME!
posted by twiggy at 9:37 PM on September 3, 2008 [1 favorite]

That's a shame about Alinea. But Chicago is a great restaurant town and if you want high end and high concept you could try Charlie Trotter's.

If I had to pick one restaurant to send you to, however, it would be Sweets and Savories. It has the best prix fixe deal in the city, the food is fantastic, the service is great, the ambiance cozy and romantic, and its pretty obscure and unique.

The architectural boat tour is good. Another choice is doing one of the bike tours, where you ride along the lake shore, through the ritzy and beautiful Gold Coast, and through Lincoln Park and Museum Park.

Also, n-thing Millennium Park, the Signature Lounge, Kingston Mines, the Green Mill, and I'd recommended the Museum of Contemporary Art over the Art Institute.
posted by AceRock at 8:58 AM on September 4, 2008