Help two New Yorkers navigate 3 days in Chicago
April 11, 2012 9:24 AM   Subscribe

We're going to Chicago this weekend! Despite a 50% chance of rain (BOO) I am determined to have an awesome time. We will be staying in Wicker Park and plan to rely mainly on bikes and the L to get around. We aim to eat, shop and explore. Where do we start?

My husband and I (two New Yorkers) are headed to Chicago. I love Chicago, but while we have a few touristy things on our plate, I'm mainly interested in seeing the neighborhoods. There is a teeny, minuscule chance I might convince my New York-lovin' husband to move here, so any and everything that reveal what life is like in Chicago for non-tourists, good or bad, would helpful for both of us.

We're pretty lazy New Yorkers - we go to the theater and shows and whatnot, but it took us years to do Top of the Rock, and we still haven't seen the Statue of Liberty up close. So a boat tour of Chicago may likely be our one, requisite touristy thing.

My husband and I like:

-Thai Food, Vietnamese Pho, BBQ, Southern food, Soul food, hole-in-the-wall cheap food, pizza. We are unabashed carnivores.
-laid-back and/or atmospheric bars, bonus points for outdoor seating, good cocktails or extensive beer selections
-safe, scenic biking routes
-green spaces
-clothes shopping (he is fairly tailored, I am a dressaholic)
-fun neighborhoods


We're staying in Wicker Park and have a very knowledgable friend who will show us around WP and Logan Square.

This is our itinerary so far:


930AM: Land at O'Hare, take blue line to Wicker Park
12PM: boat tour kicks off at Navy Pier
130: Boat tour is over, we will rent bikes nearby if it's not raining
If the weather permits biking around, where do we go next? We will likely be hungry for lunch, shopping, bookstores, fun neighborhoods. If the weather is sucky, I'd probably keep the traveling a bit more limited to only 1-2 neighborhoods.
730PM: drop off bikes at the apartment, take L up to Sticky Rice in North Center
830PM: Dinner at Sticky Rice
11PM: Cab it over to Neo-Futurists in Andersonville
1230: Cab back to Wicker Park, meet up with friends at Big Star

Saturday is open. We'd like to wander around, go shopping and eat lunch an awesome lunch, then preferably have dinner near Wicker Park or Logan Square. Then we'd go out to bars.

Wake up: brunch at Publican
330: take blue line to O'Hare for 530 flight

So, how do we make the most of our time in Chicago this weekend?
posted by zoomorphic to Travel & Transportation around Chicago, IL (15 answers total) 13 users marked this as a favorite
Best answer: Saturday, go to Longman & Eagle in Logan Square for dinner. Great food, cocktails, and beers.
posted by smich at 9:31 AM on April 11, 2012

My two favorite things in Chicago are the Lincoln Park Zoo which is free, but not necessarily a great idea if it's raining, and going to the top of the John Hancock Observatory.

Lincoln Park is far and away my favorite neighborhood in Chicago.
posted by MidsizeBlowfish at 9:33 AM on April 11, 2012

Best answer: Yes, the architectural boat tour is an absolutely must, must, must. I am not talking about the boat tour on the lake; I am talking about the RIVER boat tour that starts near the ol' Chicago Spire site, not Navy Pier.

Ride public transportation for FUN, as an activity in itself, not just as a way to get from one place to another; it's different enough from a NYC public transportation experience.

Another vote to hang out in the Lincoln Park area.
posted by TinWhistle at 9:42 AM on April 11, 2012 [1 favorite]

Best answer: I don't have anything specific to offer other than to reinforce that you're going to love the Publican. I've not been there for Sunday brunch, but If you're up for beer that early, their house blended "Lambic Doux" is exceptional every time I've sampled it.
posted by teriyaki_tornado at 9:53 AM on April 11, 2012

What part of NY does your husband love? That will have a big impact on the neighborhoods you should visit in hopes of convincing him.

That being said, there are a couple of places that are worthwhile no matter what part of town he'd like. I recommend The Green Mill, almost universally. It gets SRO earlier than I recall in years past. I think we arrived there around 9:30 and got in without a wait. When we left less than an hour later there was a line around the corner. Consider sticking this in somewhere on your jaunt to Andersonville. Earlier you're more likely to get a place to sit. Later you're more likely to love the vibe.

North Pond (website is down at the moment, check yelp?) is one of my favorite places to enjoy dinner in Chicago. They have brunch on Sundays, but otherwise it's just dinner.

Most of the places I know to send men shopping have closed since I left Chicago so I'll leave that to others.
posted by FlamingBore at 9:56 AM on April 11, 2012

Lunch at Birreria Reyes del Ocotlan in Pilsen could potentially be one of the best meat-related experiences of your life. (As a side note, I find the fact that Google Streetview managed to get inside the restaurant extremely alarming.) You could follow it up with a walk down 18th to the nearby National Museum of Mexican Art, which is free and really good, and you'll see a part of Chicago most tourists skip. There are also a number of vintage clothes stores on 18th. You can get there from Wicker Park via the Damen bus, or from the Loop via the Pink Line.

If you decide to do the Lincoln Park Zoo instead (which isn't a bad decision even if it's raining -- it'll be less crowded and the best exhibits are indoors anyway), get lunch at Del Seoul (2568 Clark). The kalbi tacos are fantastic and I would sell a lung for their slaw recipe.

You might already be aware of this, but the Violet Hour is literally across the street from Big Star and serves up hella fancy cocktails. "Laid back" it's not, though.

The Map Room in Bucktown is well-known for its fantastic beer list, which changes constantly.

The lake shore trail is the obvious choice for a scenic bike route, although it's mobbed on nice weekends. The part south of the Loop is usually less crowded. Humboldt Park is beautiful and close to where you'll be staying.
posted by theodolite at 10:11 AM on April 11, 2012

Quimby's, Unabridged, Women and Children First, Seminary Co-op and 57th st for bookstores.
posted by brujita at 10:27 AM on April 11, 2012

Best answer: lunch, shopping, bookstores...

If you're renting the bikes near Navy Pier, there'll be a few independent bookstores within striking distance:

Open Books (213 W. Institute Pl.) is the fund-raising outfit for a literacy nonprofit. Broad selection, charming decor. Drawbacks: it's sited just a little out of the ways of anything else you might want to visit, although the nearby River North neighborhood has lots of dining options.

After-Words (23 E Illinois) is a double-decker that sells both new and used. It's right next to Jazz Record Mart, a crate digger's paradise.

There's a Powell's Bookstore (historically connected to but presently unaffiliated with the more famous Oregon Powell's) at 2850 N. Lincoln. They have a great selection of marked down academic and specialist titles - particularly in medieval history - and a very decent inventory of literature and poetry. There are a lot of dining options in that area; if you think you'd enjoy Chicago-style stuffed pizza, I can recommend the spinach deep dish at Bacino's, 2204 N. Lincoln, just north of Oz Park.

The famous Seminary Co-Op, one of the best bookstores in the country, is way the hell down in Hyde Park. If you're not planning to visit that neighborhood (which also hosts the splendid South Side headquarters of Powell's), you might pop into their concession in the Newberry Library. The Library itself is a glory, although it's not really set up for casual touring.

If either of you read in French, Italian, Spanish, or German: Europa Books, at 832 N. State.

Selected Works is tucked away on the second floor of the Fine Arts Building, one time headquarters of the Studebaker Corporation (410 S Michigan). Tall, dusty shelves, a free-roaming rambunctious cat, and the fact that the store's only accessible by the last manually operated elevator in the city place ahead it of all rivals for genuine bookstore atmosphere. Millennium Park, Grant Park, and the Art Institute are all close at hand.

Not a bookstore, but damn near mandatory: the Poetry Foundation's two-story poetry library. It's open to the public from 11 to 4 on Friday.
posted by Iridic at 10:54 AM on April 11, 2012 [2 favorites]

Best answer: Saw your above the fold and came in here to tell you to go to Big Star, so I'm glad to see that's already on your schedule! I miss their tacos so, so much.

Also in Wicker Park is the fabulous Myopic Books, which is not to be missed. If you do head down to Hyde Park to check out Powell's, the Seminary Co-op, and 57th street books, be sure to also go for a walk around the Point, which is the small but lovely lakefront area there, and part of the delightfully flat and wide bike path that stretches along the whole lakeshore, all the way to Indiana. It's a pretty terrible neighborhood for any other kind of shopping, but the bookstores are excellent and it is a really pretty bike ride down there from the North side.

You might also want to visit the Hopleaf while you're in Andersonville, but it might be too packed to be fun.

And Iridic knows of what he speaks! That is an excellent list.
posted by dizziest at 11:20 AM on April 11, 2012

I second (third?) the Map Room and Seminary Co-op.
posted by onepot at 12:03 PM on April 11, 2012

Best answer: Depending on your tolerance for standing in line, The Violet Hour is potentially the worst place to go on a Friday or Saturday. YMMV, but I live right down the street and get to see big lines of people standing in the cold for hour+ waits every single weekend.

On the other hand, it is a great place (I prefer to go early in the week). They open at 6 if you want to try to jump the wait.
posted by shakespeherian at 12:55 PM on April 11, 2012

Best answer: We will be staying in Wicker Park and plan to rely mainly on bikes and the L to get around. We aim to eat, shop and explore. Where do we start?

In that neighborhood, I like:
Una Mae's
Store B
Sir & Madam
The Wormhole
Bleeding Heart Bakery & Cafe

Around Logan Square, you might like Wolfbait and B-Girls, all local designers. I couldn't find a ton of boutique shopping immediately around Logan Square. But I heartily second Longman & Eagle, especially the duck egg hash and the bourbon list, in addition to their beer list. They do a good brunch, too.

-Thai Food, Vietnamese Pho, BBQ, Southern food, Soul food, hole-in-the-wall cheap food, pizza.

You will probably love the LTHForum's Great Neighborhood Restaurants list.

We are unabashed carnivores.

If you find yourself near Michigan Ave after the boat tour, head into Purple Pig for a late lunch.

-laid-back and/or atmospheric bars, bonus points for outdoor seating, good cocktails or extensive beer selections

The Violet Hour is excellent, but as mentioned above, very popular. At a minimum checkout whatever artwork they have on the scaffolding at the moment. The entrance is speakeasy-esque and looks like construction work. I find it to be similar in vein to a large Death & Co or Milk & Honey in NYC.

For something you absolutely cannot find in NYC's cocktail scene, with a nice atmosphere, outdoor seating, and experimental, modern (and pricey) cocktails: The Aviary. They are currently serving a selection of drinks and bites both from their catalog as well as some from the now-shuttered el Bulli (with Ferran Adria's blessings, of course). They also serve an old fashioned inside of a big ice sphere that you need to break to enjoy, a drink in a "porthole" device that changes flavor over time due to botanicals sitting in the liquor, and more.

Since you like beer, in addition to the Publican, Hopleaf, Longman & Eagle, and the Map Room, also look into The Bristol and Owen & Engine.

930AM: Land at O'Hare, take blue line to Wicker Park
12PM: boat tour kicks off at Navy Pier
130: Boat tour is over, we will rent bikes nearby if it's not raining

Bear in mind that Chicago is much more geographically spread out than Manhattan. You might want to eat lunch before you hop on your bikes. However, there's also not a whole lot of quality dining options near Navy Pier, it's kind of like NYC's South Seaport.

Also, I find that Google Maps also consistently underestimates walking times in Chicago.
posted by kathryn at 3:32 PM on April 11, 2012

Best answer: Definitely go to the Green Mill (Lawrence and Broadway, by the Lawrence stop on the Red Line). That's my top recommendation for any visitor to Chicago. It's like stepping into the 1940s (which is when it was last renovated). It's the oldest continuously running jazz club in the world.

Also, for your tailored husband, check out Haberdash (607 N. State St., in the River North neighborhood) for a fantastic curated selection of men's clothes.

Finally, here's a nice walking tour: go from the Belmont Red/Brown Line station east to Broadway, then south to Diversey, then south on Clark to Fullerton, then east to the lake / Lincoln Park Zoo.

Chicago is awesome!
posted by adrian_h at 7:41 PM on April 11, 2012 [1 favorite]

11PM: Cab it over to Neo-Futurists in Andersonville

Note about the Neos: The show is cash only and first-come first-serve, so I'd recommend showing up between 10:30pm and 11pm. Doors open at 11pm, but there's normally a line outside the theater by that point. If you hate waiting in long lines, memail me. I work there and I can get you reserved seats.

Also, if your dinner ends early, I'd be happy to meet you for NeoFuturists drinks at Hopleaf or Konak. Both those bars are right around the corner from the theater.
posted by lholladay at 2:58 PM on April 12, 2012

Response by poster: I AM EXCITED EVERYONE. Thanks for all of the advice, it's been almost silly picking our Best Answers. We are definitely planning on Longman & Eagle for dinner on Saturday, hitting up the architectural boat tour, have all the bookstores saved on Google Maps, and have Wolfbait, Haberdash and other stores on our lists of places to drop cash.
posted by zoomorphic at 8:52 PM on April 12, 2012

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