fun things to do alone in Chicago?
July 1, 2008 8:31 AM   Subscribe

What should I do alone in Chicago?

I'm going to be in Chicago July 17-22 with my boyfriend. We already have plans to go to the Art Institute, bum around Michigan Avenue, go to the Signature Lounge, see Too Much Light Makes the Baby Go Blind, eat at delicious restaurants, wander through some neighborhoods, and go to some parks.

What I am looking for is something (inexpensive) to do on Saturday while my boyfriend is hipstering around the Pitchfork Music Festival and for other times when he is hanging out with some of his friends that I'd prefer not to spend too much time with (I can't handle hours of indie-rock talk!).

Suggestions for interesting places to sit and read would be nice if nothing else comes to mind. Also, I wouldn't be opposed to renting a bicycle and biking around the city but I am scared of super busy streets so bike route suggestions would also be welcome.
posted by mustcatchmooseandsquirrel to Travel & Transportation around Chicago, IL (21 answers total) 9 users marked this as a favorite
Best answer: You can bike all the way up and down the Lake Path east of Lake Shore Drive. There are plenty of bike shops that are close and would provide a good opportunity for this.

Every time I'm in Chicago I don't miss Maza, which is amazing Lebanese food at a good price. If you like TMLMBGB, you can always go a little more upscale and try Second City.
posted by onalark at 8:41 AM on July 1, 2008 [1 favorite]

You could go to Oak Park, pick up a visitors map for about five bucks, and check out all the Frank Lloyd Wright designed houses.

This would be the bare-bones tour -- the guided tours sponsored by the visitors center are more expensive. The map would just give the street addresses where different houses are and that's it, and you'd just be able to stand out front on the sidewalk and see them. So it ain't for someone looking for exhaustive commentary, history of the houses, or even being able to go in. But if you just want to check out the exteriors and stand there saying "ooh, yeah, that's a cool window" then this is the way to go.

(I'm also convinced that you can SEE new-architect-jitters on the first house Wright designed all by himself -- everything else is pretty minimal in terms of ornamentation, but there's this one house that looks like he just got nervous and kept adding stuff to make it look Impressive.)
posted by EmpressCallipygos at 8:44 AM on July 1, 2008 [1 favorite]

Oh, and seconding the lake shore bike path. You can also rent bikes at Navy Pier.

The Field Museum, the Planetarium and the Aquarium are also all right near each other on the same peninsula; there's also the museum of Science and Industry that's a little further away. But you could maybe start at either the Field Museum, Planetariam, or Aquarium, have your boyfriend meet you there and you hit the next two together.
posted by EmpressCallipygos at 8:47 AM on July 1, 2008

Field Museum!
posted by k8t at 9:09 AM on July 1, 2008

Also, The Lincoln park conservatory, the Lincoln park zoo, and the Garfield park conservatory are all free (or donation only) and are all on train lines.
posted by Craig at 9:09 AM on July 1, 2008

Best answer: You can rent bikes at the Millenium Park Cycle Center on Randolph Street, which is much easier to get to than Navy Pier. The people at the cycle center will supply you with a map and are really friendly. It's not cheap to rent a bike in Chicago, but riding on the lake path, like many have suggested, is really great. I suggest you go south -- it's just as pretty, but there are far fewer people down there, and you get to go around the aquarium and are very close to the water for most of the trip. Going north is not as fun, in my opinion.
posted by k8lin at 9:13 AM on July 1, 2008 [1 favorite]

Best answer: By bike you can easily navigate around town. For just general hanging out you may really enjoy Lincoln Park (the park, not necessarily the neighborhood.) There are bike maps which can get for free from the tourist office or any bike shop.

Right now the ultimate leisurely bike trip around town is out to Northerly Island which affords really amazing views of the city. It's a short ride south from the Field Museum/Planetaram/Shedd Aquarium.

Let me know if you have trouble locating a bike.
posted by wfrgms at 9:19 AM on July 1, 2008 [1 favorite]

Best answer: Everyone's suggestions are excellent, the museums are fantastic. I'll add a few of my own second-tier suggestions...

Check out the Harold Washington Library, if you're so inclined. A massive, bookalicious tower to literacy in downtown and not to shabby to look at, either.

Union Station, a little west of the river on Jackson Avenue, has a nifty beaux-arts feel to it. The new section underground is strictly utilitarian, but walk through the Great Hall and pretend that you're in The Untouchables. My baby!
posted by burnfirewalls at 9:24 AM on July 1, 2008

Best answer: I had a great time alone in Chicago a year or so ago. Here's my TravelFilter entry about it.
posted by Miko at 9:25 AM on July 1, 2008 [2 favorites]

Wicker Park is a nice place to sit and read, with good people watching. There are also outdoor cafes on Division Street west of Ashland. There's great people watching there as well, although all the hipsters will probably be at Pitchfork. There's a used bookstore not too far from there where you can pick up reading material:

Myopic Bookstore

The lakefront biking is great, but I second the idea to go south of the river - north gets really really crowded.

The architectural boat tours on the river are also pretty cool. It's a fun way to see the city and the gorgeous architecture. There's a few different companies and I think they're pretty much the same deal. One leaves from Navy Pier - you'd probably want to go on the early side to be sure to get tickets for a decent time.
posted by slo at 9:32 AM on July 1, 2008

Best answer: I like the Cultural Center. Across Michigan Avenue (eastwardly) from north Millenium Park. Used to be Chicago's public library, lots of ornate early 20th century mosaics on the walls, nice view of Millenium Park. Lots of, often free, public events like concerts and lectures.
posted by goethean at 10:11 AM on July 1, 2008

Westerly! not easterly! Sorry!!

The map was upside-down in my head.
posted by goethean at 10:20 AM on July 1, 2008

You could ride your bicycle to the John Hancock Center and eat on the 95th floor. You get lunch for the same price you pay to go up to the observatory at the Sears Tower. Contrary to what you would expect, it is not too expensive for lunch (about 10-12 bucks). Admittedly, the food is pretty heavy, but generally good. There is a family of peregrine falcons that roost on top of the building that you may see flying past the window. The view's not bad, too.

I second the trip to Oak Park. There is a high density of Frank Lloyd Wright buildings and a nice park you can sit and read in called Scoville Park right by the Oak Park stop on the el. (1 block north) Even the water fountain is designed by Frank Lloyd Wright. It would be a good break from high density urbanity. You can take the Green Line out there and you'll be right in the middle of town. The aforementioned Garfield Park Conservatory is also on the Green Line (there is a stop called Conservatory).

They just reopened the Tiffany-made stained glass skylight at the Cultural Center. It's beautiful.

Come to think of it, I guess I just assumed you knew about Millenium Park! You guys should definitely spend some time there/spend some music there. You might even see if the Grant Park Orchestra is playing. Man, a good long walk down Michigan Avenue would be a lot of fun. You could walk from the John Hancock to Millenium Park. Nice!

Anyway, have fun in Chicago!
posted by peetle at 10:32 AM on July 1, 2008

You're female, I'm guessing? If so, please stay WITH the crowds on the bike paths and the lakefront. It's not like you're going to be mugged if you dare venture away from the Loop, but just use common sense and remember you're in a big city with big city crime.

The mom in me also wants to tell you to wear clean underwear in case you get hit by a bus.

Get yourself a couple of trashy novels and go to the beach.

Go north to Evanston and wander around the Northwestern University campus.

Go window shopping on Michigan Avenue.

Is there music YOU like? Tons of clubs. Try Buddy Guy's Legends in the South Loop for blues. They don't care if you're by yourself - they'll take care of you.
posted by SuperSquirrel at 10:56 AM on July 1, 2008

If you're into architecture, tickets to the Chicago Architecture Foundation's
walking tours are less pricey than their boat tours (although the boat tours are pretty great in the summer).

As mentioned above, Wicker Park is a great neighborhood for people watching, shopping, and getting a taste of the city away from your standard tourist attractions. It's also pretty easily accessible by bike from downtown, just a straight shot up Milwaukee Ave (which has bike lanes/marked shared lanes all the way up). You can sit and read in the park, grab some tasty veggie food at Earwax, or grab a cup of coffee and some macaroons at Lovely (not in Wicker Park, but on your way there if you're biking up Milwaukee).

Have a great time!
posted by eliina at 11:09 AM on July 1, 2008

I can't really add anything, lots of Chicago info all over the green. Just wanted to pipe in and say thanks to Miko for clueing me in to TravelFilter. Had no idea this subsite (?) existed. What a great resource! And also, Miko I can't believe you were in Chicago and didn't call (not that you knew who is was then, but still)
posted by nax at 11:28 AM on July 1, 2008

who. I. was. then. It is really hard to type with your foot in a cast propped up next to the keyboard.
posted by nax at 11:28 AM on July 1, 2008

we had tried to have a meetup but the bar was closed and it sorta fizzled, there were a total of 2 of us there. I know Chicago is full of MeFites but I guess the timing was bad
posted by Miko at 11:43 AM on July 1, 2008

Best answer: One underrated fun free place is the stained glass museum on Navy Pier.
posted by EmilyClimbs at 7:55 PM on July 1, 2008

Lets put you into Chicago, as far from hipsterdom as possible (my Chicago)

On Michigan ave, do the Hancock sans the observation deck as noted above. Walk north on Michigan till you hit North Ave Beach, the 'hip' beach for all the Northsiders, complete with tons of volleyball games, drinking and lots of people showing off. It's a great time. Stop into Castaways to experience it first hand. Keep on walking up the beach, Lake Michigan is wonderful until you hit the Lincoln Park Zoo. Sweet. Once you hit Fullerton, make a left until you hit Clark... then take a right down Clark (you can stop and get a dog at Weiner Circle--best regular dogs in the city) until it splits off onto Broadway and CLark, take a right down Broadway. Now smack, you are in the middle of Chicago's 'gayborhood'-- Boystown, which is fairly diverse and an actually narrow, dense street. Take this up until you hit Addison, then make a left. You'll go a couple blocks down past and you'll see Wrigley. If there's a game going on, you'll experience a drunken part mess (which I enjoy).

Now once done here and past all the ticket brokers and drunks, you can walk down Sheffield through quaint--and super rich-- Lincoln Park until you hit Fullerton. Stop in for a beer in a uber preppy Beer garden a whole slew of them along Sheffield between Diversey and Roscoe. You can then walk by Depaul, then down Lincoln down another strip of bars and restaurants (the Student 'ghetto' bars) till you hit North. My geography is bad now but you'll want to go down Wells through Old Town. You could maybe hit up a Second City Show. I guess this is a long day.

You'll experience Chicago and be as far from hipsterdom as you can imagine.

Its roughly 3 miles, so it'll take you two hours if you do it slowly. I did this 3 years ago and decided I wanted to move to Chicago.
posted by sandmanwv at 9:13 PM on July 1, 2008

Response by poster: Thanks for all the answers! I'm not really into wandering around and looking at architecture/museums alone (it's more fun when you go with someone and can discuss it, no?) but all of the bike and random place suggestions are nice. I don't really need to put myself "as far from hipsterdom as possible" and might take the suggestion to hang out at Wicker Park since last time I was in Chicago it seemed like a cool place.
posted by mustcatchmooseandsquirrel at 6:52 AM on July 2, 2008

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