Travel Guide Needed…

I need your help. Well, I guess I don’t really NEED it, but I’d love it anyway.


Tomorrow afternoon I am headed to the Windy City for a quick weekend getaway. One of my closest friends moved there this summer and so I am flying in to see her new digs and check out her city. This will my my first “real” trip to Chicago. What I mean by “real” trip is that I went a few years back for Book Expo America, but the only site I really took in was the McCormick Center, so I decided that trip didn’t count.

Here are just a few of the things we have talked about as possibilities:

Outings – Cubs Game, Architectural Boat Tour, Lincoln Park Zoo, Shopping (face it there will be some of that regardless of what you say)

Here is where you come in. Please share what you think I need to see/do/eat during the two days I am in Chicago?

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Lindsey has a sincere love for her precious dogs Molly and Maisy, a good red wine and the Delta Sky Club.

Please note: I reserve the right to delete comments that are offensive or off-topic.

  • rebrev

    Recommend The Moody Church – the Word is preached and the people are friendly!

  • If you like coffee, you should definitely go to Intelligentsia at 53 E Randolph. It is also close to Millennium Park and the Art Institute, both of which are great.

  • The weather is supposed to be great this weekend, so a walk along the lakefront would be fun. You can also rent bikes in Millennium Park, which would also be lots of fun.

    Intelligentsia is the BEST coffee–definitely try to get some while you're here.

    If you're shopping on Michigan Ave, eat at the Grand Lux Cafe (above Ann Taylor). A fun atmosphere and yummy!

    If the weather does cooperate, you could go up to the top of the Sears Tower or the John Hancock building. Touristy, yes, but a good view of our gorgeous city.

  • Navy Pier, Shedd Aquarium, Oprah (say hello from me)

    That's all I got. 🙂

  • Jennie Waller

    You NEED to go eat at Chicago Pizza and Oven Grinder. Their food is amazing! Pizza Pies, Mediterranean Bread, Salads. It was all delicious. They are on 2121 N. Clark St.

  • Last time I went to Chicago we went and saw The Blue Man Group – FUN FUN FUN!!

  • Chicago – I miss it so. I'm jealous you are going! I'll pitch in a few don't miss things from the food and entertainment dept.

    1 – Chicago Deep Dish pizza – Carmen's (our favorite in Evanston @ NU), Pizzeria Uno & Due, Giordano's or Gino's East. Gino's East is probably the most unique experience. Giordanos seem to be all over the place. All of them have great pizza that is unique to Chicago.
    2 – Either of the Rick Bayless restaurants-Frontera Grill or Topolobampo on North Clark Street. It's Fine Dining Mexican food like you have never ever had. We had a fantastic meal @ Frontera last year. FYI – Rick won the Top Chef Masters competition this summer.
    3 – John Hancock Tower AT DUSK. This is a great view of the city any time and the lake is just beautiful this time of day. Good for a quick 30-60 minute side trip and will be a lasting strong memory of Chicago. Also, it's right next door to Water Tower Place (Mega mall for shopping) and sits on the end of miracle Mile, so it's a great place to hit on one end of a long stroll down Michigan.
    4 – The Backroom on Rush street – Great late night jazz. I have visited this place several times (once with Terry F) and never failed to have a great night of jazz with terrific local talent.
    5 – The Green Mill on Broadway – This is a locally famous Jazz club (with an Al Capone connection) that is a little further north above Wrigleyville. The local acts are all very good. In March, we just dropped in and caught a string band (acoustic guitars, fiddle, bass and accordian) that was astonishing. it was a wild mix of Klezmer, Django Rheinhardt Brazilian Jazz that was really really great.
    6 – Jazz Showcase @ Dearborn Station – This is a world famous jazz club. I saw Ray Brown here (one of Miles original sidemen) and a number of other big name acts. Your timing is good, because Jason Marsalis Vibes Quartet is playing there through the weekend. Certain to be great, and likely to be sold out, so call if you want to go.
    7 – Second City Improv – They have two theaters and are always a stitch!
    8 – Art Institute – If you have never seen the George Seurat "Sunday Afternoon on the Island of Grande Jatte", it's worth the price of admission. Of course, there are so many Master works there, you can spend hours and hours!
    9 – Walking Grant Park – I'll second that suggestion. the weather should be just fantastic and that will be a great place to people watch.
    10 – Navy Pier – lots of touristy things, but loads of fun on a cool evening to people watch. On top of that, you might met Forrest Gump (my friend Paul Dengler works as Forrest for the Bubba Gump stores and frequently haunts that location).

    In the end, I know you will have fun!

  • Giodono's Pizza. THE BEST Chicago Style Pizza hands down. I'm going to Chicago in March for a conference and you better believe that will be one of my first meals there.

  • For great pictures of your visit, do the arcitectural boat tour and the Hancock Center. Boat tour gives a different perspective of the city…actually so does the Hancock Center.

    Take the el for some interesting sightseeing.

  • Kathleen

    You definitely need to eat some Chicago Style pizza and visit the Navy Pier. I did a skyline boat tour and loved it so that's another idea too 🙂 Enjoy your trip – I'm jealous!

  • Gary

    Visit the Sears tower, Navy Pier, go to a Cubs game (or at least visit Wrigley Field and get a tour), and enjoy yourself!! Also, go to Lou Malnatti's Chicago Style Pizza. I heard that palce is VERY good, and it's a NON-Chain restaurant too!! (I normally make it a point to try and eat at NON-chain restaurants).

  • I loved my morning stroll through Grant/Millennium Park on the Lakefront and a trip through the Art Institute of Chicago Museum on Michigan Ave. I'm told the Kingston Mines are the place for Blues music, but I didn't make it.

  • delina

    I always recommend the Chicago Food Planet walking food tour to people. It was awesome… you learn about the city, walk the neighborhoods, meet people, eat great food… you gotta do it!

  • Laura McGowan

    Le Colonial is our favorite restaurant, so you are in the know! U2 is in concert this weekend at Soldier Field and tickets are still available, so that could be a fun option.

  • Here's a unique thing to do in Chicago this weekend (Intellingentsia, Millennium Park, and the Art Institute are all in this area as well)….

  • I'm too late to contribute… but you should've gone to the U2 concert on the 12th and 13th!

    Anyways, hope you had a wonderful time!