Help me fill out my Chicago itinerary for next weekend!
April 26, 2014 10:34 AM   Subscribe

My husband and I are landing in Chicago for the first time on Saturday, May 3rd and will be there until the evening of the 5th. One purpose of the trip is to visit my husband's father, who has been living there for the last year, but the other is to explore Chicago. We are staying at La Quinta in Downtown Chicago, mainly because we got a good deal on it through Hotwire. My husband's dad lives at the Streeter, in the Near North Side area. What should we see while we're there?

Here's what we're planning to do so far, so you can let me know of anything that would fill in the blanks well:

Arrive 8 am
Taxi to hotel (Is this necessary? Would it be possible to take public transit and still avoid the crazy lines for brunch? Our hotel is about two blocks from Sears Tower.)
Brunch at 10:30 am – Frontera Grill (I am excited to try one of Rick Bayless' restaurants, but it appears that they're not open Sundays or Mondays, which limits our choices -- hence the frenzied run to brunch. We couldn't get a reservation for dinner.)
Art Institute of Chicago -- we've heard great things about this place and both love good art museums.
Chicago Architecture boat tour – 5 pm -- booked for all three of us
Sol Y Nieve – 7:15 pm dinner (reserved)
Walk back to the Streeter
Back to hotel

Walk to Maxwell Street Market and eat there -- apparently amazing Mexican food from vendors (while we're in this area, is there anything else worth exploring nearby?)
Spend more time with my husband's dad (walk to Near North Side - any route we could take that would be more interesting?)
Use Divvy bikes to ride north up the Lakefront trail, headed to Lincoln park (what should we see around here? Everyone mentions the zoo, but neither of us cares much for zoos). Jettison bikes at Divvy station
Dinner at Bistrot Margot (chosen mainly for proximity to the Second City, below. We're open to other suggestions but we need them to be extremely close to Second City since we want to be able to have dinner as late as possible, and the show at Second City begins at 7 and doors open at 6:15.)
Comedy show at Second City - Depraved New World

Go early to Willis/Sears Tower to beat the lines (a lot of people have been recommending the John Hancock building instead, but my husband really wants to go the tallest building and it's only a couple blocks from our hotel).
We still haven't figured out what to do with the rest of the day Monday. Our flight leaves at 6:30 pm. What would you suggest? We'd love to explore an interesting neighborhood or take a ride on the El, while exploring different stops, for example.

More about us: We're pretty geeky people, who like museums (in moderation), interesting architecture, good food. I am willing to travel simply to eat at a great restaurant, but to persuade my husband there usually needs to be something of cultural significance in the area as well. So suggestions of the type, go to Place X and see Y, and while you're there at at Z, are especially welcomed. My husband doesn't drink and I don't like the taste of beer, so in general we're not huge on bars (though I love interesting cocktails).

Any advice on our itinerary - filling in the gaps, telling us what won't work, as well as suggestions for Monday would be great!
posted by peacheater to Travel & Transportation around Chicago, IL (13 answers total) 9 users marked this as a favorite
I am excited to try one of Rick Bayless' restaurants

I did a program at UChicago, and speaking as someone who mostly does not eat Mexican food, once I discovered Xoco, I was instantly addicted and subsequently went there for lunch every day I had class. It gets mobbed quick, so go early or else get takeout and sit down somewhere to eat.

I'm going back to Chicago for a couple days this summer, and I have three meals already planned, Alinea and two of my favorite places that I'm dying to return to: RPM Italian, which is kind of trendy but totally worth it; and Little Goat, which is phenomenal and miles better than its upscale cousin across the street. However, most of my touring was in the evenings and I was focused on food, so unfortunately I can't speak to culturally significant spots nearby.

a lot of people have been recommending the John Hancock building instead

I got the same recommendation and followed it. It's a pretty great view, but it falls into that category of things I'm glad I did once and won't repeat. I can't speak to Sears. Good call on the architecture boat tour, by the way. It's great.
posted by cribcage at 10:52 AM on April 26, 2014 [1 favorite]

As I've recommended in previous askme's, a Segway tour is a lot of fun.
posted by Sophont at 11:30 AM on April 26, 2014

Best answer: The Museum of Contemporary Art is really fabulous. It isn't open on Mondays, but it's not far from the lakeshore trail, and pretty easily accessible by bike (and there's a Divvy bike station right near it), so you could probably make it part of your Sunday excursion.

As far as Monday, Wicker Park is a pretty great place to walk around. You can get brunch at Handlebar, go to Quimby's and Myopic books (and do other non-book-related shopping, if you're so inclined), and eat tacos at Big Star. It's also conveniently right on the Blue line, which is the train you'll take to the airport.
posted by dizziest at 11:36 AM on April 26, 2014 [2 favorites]

Near Second City: Adobo Grill (interior Mexican, great margaritas) or Old Town Social (upscale sports bar-ish, great cocktail program), but Bistrot Margot is also great.

Monday: second Wicker Park or its neighbor Ukrainian Village. Wicker Park is full of interesting shops and good food.

The MCA is fabulous.

The view from John Hancock is great, possibly better than from the Sears/Willis Tower and the bonus is that you can go up for food or drinks at the Signature Room and not pay for what is essentially an elevator trip. The Sears/Willis does have the suspended glass boxes, though, which do not interest me at all, but everyone likes different things. :)
posted by devinemissk at 11:43 AM on April 26, 2014 [1 favorite]

If any of the other attractions attached to the Chicago Citypass interest you, it would be worth it to buy them. Regular admission to the Skydeck at the Sears Tower and the Art Institute total $80, so if you were interested in, say, the Aquarium, which is great, or wanted to do the Hancock as well, it would save you some money. Plus it lets you skip the main line at Skydeck, which is awesome.

Google Maps says it will take just under an hour to take the train and walk to your hotel, and then about 20 minutes to walk to Frontera. A taxi will be more expensive, and may honestly take just as much time depending on traffic.

I would agree that spending the day exploring a neighborhood would be fun. Wicker Park is good, and I just spent a Saturday in Lincoln Square, which has a bunch of cool little shops and so forth.
posted by papayaninja at 12:56 PM on April 26, 2014

Nuevo Leon is amazing Mexican and cheap. Very crowded on Sundays but worth it. Pilsen has tons of street art murals around there. In addition the Mexican museum of Art is close by. (I'm not sure of its hours though. It is always free)
I'd take the train downtown and catch a bus to the hotel. Google maps has a public transportation option (the little bus icon)that will show you the way and give you estimated times.
For bunch I'd recommend Shuba's on Southport and Belmont. So good.
posted by AlexiaSky at 3:25 PM on April 26, 2014

There also is a walking architecture tour that goes through Pilsen. Many of the buildings were built in the early 1900 (or late 1800) . It's pretty cool.
posted by AlexiaSky at 3:28 PM on April 26, 2014

Best answer: Just a few quick thoughts:

I generally don't like zoos either, but if you want to zip into the Lincoln Park Zoo and not spend all day there, visit the Great Ape House.

Nearby, the Peggy Notebaert Nature Museum has a cool butterfly haven where you can stand among a zillion exotic species of them in a lush tropical environment.

If you're interested in Chicago history and architecture, you pretty much have to visit Graceland Cemetery. Sometimes I drive in there just to gaze again upon Louis Sullivan's perfect Getty Tomb (1890), said by some to be the birth of modern American architecture. (Sullivan's grave is also there.)

Finally, looking forward, if you happen to be at the south end of the Mag Mile, note the Realtor Building, across the street from the Tribune Tower and next to the Wrigley Building. Not because it was made semi-famous as Bob Newhart's office, at 45s in this clip from the show's opening, but because in the next five years it may give way, along with the block behind it, to a 90-storey tower and Rockefeller-Center-like complex. (Negotiations continue, and an architect has been selected, but no deal has yet been inked.
posted by Short Attention Sp at 4:24 PM on April 26, 2014 [1 favorite]

Taxi to hotel (Is this necessary? Would it be possible to take public transit and still avoid the crazy lines for brunch?

What airport are you flying into?

The area around the current iteration of Maxwell St. Market is low-rise industrial and feels very spread out. I'm not saying you couldn't walk it, but there are much more interesting places to walk. The market is there because there's not much else there. There's are a couple of Divvy stations nearby; I suggest you take advantage of them. Or skip the market and go to La Chaparrita Grocery on Monday (closed Sunday), take the Pilsen tour, and go to the National Museum of Mexican Art.

On Sunday, take the #6 bus to the Museum of Science and Industry, then check out the Hyde Park Art Center. Tour the Robie House. Have lunch at Medici, an old-school Chicago pizza joint.

Ok, that's too much for Sunday. Skip the Museum.

If you could stand a bar, an interesting place for a drink after Second City is the Old Town Ale House. You might snag a bar stool that John Belushi or Chris Farley once sat on, and it probably hasn't been cleaned since then.
posted by hydrophonic at 4:53 PM on April 26, 2014

If you're looking for something to do Saturday night, the Reader and Timeout have listings. CIMM Fest is happening; there are a lot of interesting things on the schedule.
posted by hydrophonic at 5:02 PM on April 26, 2014

Response by poster: Thanks everyone for your inputs! We've decided to explore Wicker Park/Ukrainian Village on Monday, as several of you suggested. We're also going to skip the taxi to the hotel on Saturday and take public transit - it will also give us a chance to get oriented to the El. Depending on the weather on Sunday (which doesn't look great right now), we might do the MCA too. And thanks for the tip about the butterfly haven, Short Attention Sp, that looks great.
posted by peacheater at 2:56 PM on April 27, 2014 [1 favorite]

Response by poster: I'm marking this question resolved, but if anyone sees this later and wants to add something, please do!
posted by peacheater at 2:57 PM on April 27, 2014

So the benefit of the lincoln park zoo is it's free. So it's no big deal to walk through it while you're strolling through lincoln park. The park itself is pretty giant, so just walking around can be enough to do there.

Down at the south end of Lincoln Park is the Chicago History Museum. I like it, and would recommend it to people interested in learning Chicago History.

I'm a big fan of the divvy bikes, but I'd recommend paying attention to the clock while you're doing it -- you want to check the bikes into a station every 30 minutes to not get charged extra. It's not too hard to do, but not always obvious to people new to the system.
posted by garlic at 11:05 AM on April 28, 2014

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