Post # 1
Chicago bees, I would LOVE your recommendations for how to fill a weekend in Chicago. At this point all I have are plane tickets.
I’d like to find a hotel within walking distance of some good museums, yummy places to eat and drink, and get some suggestions on what to see while I’m there, and thought I would ask you ladies first!
Post # 3
I’m not from Chicago, but I make my way there quite frequently :).
Unless you’re a real history buff, the Field Museum just isn’t that interesting. The Shedd Aquarium is kind of cool, and that’s from someone who hates fish with an odd passion.
Make sure you go to the Art Institute. They have American Gothic, but also a lot of other amazing artists!
Visit the Bean (Cloudgate) in Millenium Park! It makes for some really fun photos.
My favorite pizza is Giordano’s, but wherever you go, make sure it’s deep dish!
As far as shows, the Shakespeare Theatre at Navy Pier is very good, and Blue Man Group is obviously really fun. There’s a really expensive seafood restaurant on the Pier, and I forget what it’s called, but it’s awful, so don’t waste your time going there.
If you’re trying to stay low-budget, a friend and I stayed in the Travelodge that’s located right off the Mile. Great location, and it was about $125 or something? Let me know if you need any other recommendations!
Post # 4
Wooo! What a wonderful way to spend a weekend! I love my city and love to help out people visiting!
For hotels, look for deals at the Swissotel (they tend to have some good ones and it’s a great location) but anywhere within a few blocks of Michigan Avenue and an el stop is a good call. There are a lot of hotels so if you do hotels.com and expedia you should be able to get a deal without sacrificing quality or location.
For how to fill a weekend, I would definitely plan to hit up the Art Institute and Shedd Aquarium. Those are in my top five chicago sights. If it’s nice out, rent a bike or take a run on the lakefront path – that’s one of Chicago’s top attractions right there. The Architecture Tour (run by the chicago architecture society) is a great cruise down the Chicago river that is a blast even for natives. The Sears (Willis) Tower is fun if it’s a clear day and you want to see EVERYTHING – but if you really want to have a good time and a view go for some crazy overpriced cocktails to the Signature Room on the 99th floor of the Hancock Tower (go right at dusk so you skip the lines but still get to see the view at night – oh, and don’t leave without taking a trip to the ladies restroom, just trust me on that one).
Catching a baseball game at Wrigley is generally expensive, but also generally worth it. Sox Park is fun too (with much better food and drinks). Shopping on the Mag Mile is fine but crowded with tourists. If you want some more entertaining shopping experiences head out to one of the neighborhoods (i.e. Wicker Park or Lincoln Square) to see more of where the locals do their thing.
If you want to see a comedy show head to Second City in Old Town. They are a feeder for Saturday Night Live and it’s a blast. For plays go to Steppenwolf Theater – the theater is a good size and it really allows you to feel intimacy with the actors.
For food, well the city is pretty much going to give you anything you could possibly want on that score. Check out reviews on Yelp before you go anywhere in the Mag Mile area, because you’ll get much better prices for better food if you do your research. Rick Bayless’ restaraunts are near Mag Mile and in high demand and everyone loves Quartino. But if you want to be adventurous there are endless options. Again, a little time doing research into Chicago food and you’ll be enjoying yourself completely. I’m going to put a special word in here for Kuma’s (long line so maybe not a good idea on a weekend trip), The Publican, Havana Libre and XOCO (go at off peak hours – like 2-3 pm and the line should be shorter).
Let me know if you have more questions! Happy to help.
Post # 5
Palmer House Hilton is great. I love that hotel, and they have tea time. 🙂 Call them to make reservations after checking hotels.com or Orbitz. Palmer is in walking distance of the mag mile. Have breakfast at Yolk, on Michigan ave close to Roosevelt. Awesome place. You can walk to the museum, aquarium, art institute, etc. from there. Shopping on thee mag mile is fabulous, hop on a carriage ride near Water Tower and check out the Ghiradelli’s ice cream – best hot fudge sundae ever!
Post # 6
For sights, I second @jolee – the Art Institute is fantastic. (If you know anyone who lives in the area and has a library card, they can also check out free passes to any of the museums in the city). You should also visit Millenium Park and the Bean, and the top of the Sears Tower (now known as Willis Tower) has a great view of the city on a clear day. @iRun2004’s suggestion of the Architecture Tour is a great one as well. You get to see the famous buildings and get a real feel for the city.
If you’re into food, I recommend a quick trip to Greek Town, or if you want real Chicago pizza, try Pizzeria Uno or Lou Malnati’s (with butter crust!).
Post # 7
Definitely Art Institute! I still adore it and I live here. What are you interested in? Where do you like to stay when you visit? The Loop/Gold Coast area is the most touristy and great if you like sightseeing. But our public transit system is great, and there are almost always cabs available in many of the neighborhoods like Lakeview/Lincoln Park.
We live right by Lincoln Park the park (and the neighborhood) and it’s a lot of fun, as is the zoo, which is free. I adore the shopping in Wicker Park/Bucktown – there are a lot of boutiques worth hopping into, like Eskell and Roslyn. Be warned, many are closed on Mondays.
Wrigleyville is very college town-y and sports bars abound. If you want to live like a local, one of my favorite things around here is Sunday brunch. Places on Broadway abound and the patio dining is a must. Also, Molly’s Cupcakes on Clark = total love.
There are a few amazing hotels around here, too, so if you’re not looking for Loop love check out places like the Belden Stratford or the Willows. It is a real treat, however, to stay someplace like the Hyatt where you get a wonderful city view.
Post # 8
We were there for a wedding over memorial day weekend and met up with my good friends who came down from Milwaukee….we ate together at the Cafe at Spiaggia. OMG it was seriously insaley good.
Definitely go if you can.
Post # 9
Architecture tours on the river are by far the best way to see a lot of the city – definitely don’t miss that!
http://www.metromix.com will help you find restaurants in various neighborhoods, cuisines, price ranges.
Post # 10
Wow just saw all these new replies! Thanks everyone!
Post # 11
Thought I would let everyone know the winner for hotels: Swissotel. Some bad reviews on Trip Advisor scared me away from the Palmer Hilton, though that was our original top contender.
We will definitely be hitting up as many of these places as possible. They all look fantastic!
Post # 12
Darling Husband and I went a year and a half ago to visit my sister.
We both LOVED the aquarium. We saw a show at second city, and spent some time just walking downtown. We also walked the waterfront from the planetarium to Navy Pier. In february. Brr. Also, find a good local place for chicago style pizza. Fantastic!