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?
posted by peacheater to Travel & Transportation around Chicago, IL (13 answers total) 7 users marked this as a favorite
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!