Plan My Vacation For Me, Would Ya?

March 9, 2011 at 7:00 am 25 comments

Stephen and I are going to Chicago for about 5 days this summer. I’m not going to tell you when we’re going because I don’t want you to break into my house and steal all of my hand-me-down furniture and our DVD/VHS combo. So we’ll just leave it at: This summer.

Here are the issues. We’ve never been to Chicago. We have about 2.5 days to do what we want, then we’ll be in a suburb of Chicago for a wedding and all the wedding festivities. So we need to FRUGALLY fit in as much fun as possible between Wednesday morning and Friday noonish. We’ll fly in on a Tuesday evening so we have a full day on Wednesday.

Here are some details. Any help, thoughts, feelings, or advice would be so very appreciated:

We’re going to go to a Cubs game one evening (not because I like the Cubs, Heavens no, but because I like baseball and want to go to Wrigley) and Stephen is interested in some sort of mob tour. We like food, but not seafood.

We’re flying via Hobby so that means we’ll fly into Midway. I have no idea what that means as far as our location goes. (I know I could look that up… and I will. But you’re so much better than Google and your advice will be so much clearer.)

I’ve been told we should rent a car. Yes? I had always imagined Chicago to be a lot like New York where people just take cabs and public transportation everywhere. Am I wrong?

I was hoping to use Expedia or one of those types of sites to book our flight and hotel. We’ll only need a hotel in Chicago for like 3 nights, then we’re heading to a suburb for two more nights. So our flight home date will be different than our check out date. Can those sites handle that? I would imagine so. Do they have people you can call to walk you through the process?

Where should we stay? What do we have to do? Where to we have to eat?

I need to download a map so I can figure out the city. So if you have recommendations, can you let me know what part of the city you’re talking about?

Thanks so much. Feel free to pass this along to any Chicagoians… Chicagans… Chicagos.. Chicago people.

(Edited to add: No, we will not be taking Jansen with us. I don’t know how I’ll be away from him for 5 days, but I’m going to try.)

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Ten on Tuesday (70) This Is Not The Diary Of A Wimpy Kid

25 Comments Add your own

  • 1. jen  |  March 9, 2011 at 8:45 am

    i LOVE chicago! Wrigley field is awesome! i would suggest trying to stay at a hotel on lakeshore drive, lake michigan would be your view which is gorgeous and close to the museums such as the museum of science and industry, field museum and shedd aquarium…all very cool places. also check out navy pier and perhaps take the cute baby on the ferris wheel which offers spectacular views. just go have fun, its a great place and i would rent a car, there are cabs and a great commuter trains, but i think with a baby it might be easier to have a car. sorry for the ramble, just go have fun it the great city of chicago!!!

  • 2. Priscilla  |  March 9, 2011 at 8:53 am

    Navy Pier is a great tourist spot. You will be downtown for that and there are LOTS of good pizza places. For that matter, Chicago has wonderful ethnic food. If you can afford it, the architectural boat tour of Chicago is fascinating for both architecture and the history of Chicago…but not with a baby! Grant Park and Millennium Park are downtown and free. Trains are dependable, so that is an potion. DO stay downtown. Go to sites such as TripAdvisor and read the comments people leave about hotels and such.

  • 3. April  |  March 9, 2011 at 8:56 am

    I’m not from chicago, but I went for taste of chicago two summers ago and it was awesome. Awesome! I don’t think you need a car – the public transit system is simple to navigate and very clean. And this is coming from someone who lives in a no-public-transit place and had never ridden a city bus before that trip. Bring an umbrella stroller for the baby so it’s easy to collapse. The aquarium was awesome (seriously, I’m also not much for sea life), and there’s a children’s museum at the pier.

    We stayed at the Knickerbocker, because we got a great rate on one of those travel websites and it was beautiful and very old school.

  • 4. April  |  March 9, 2011 at 9:01 am

    Oh yes, ethnic food! I can’t really point you to most of the places we ate, but I still dream of the pad-see-ew I had at a thai restaurant called silver spoon. And there is a tapas place called 1492, and a wine bar next door… Oh, take me with you, please??? I pack light …

  • 5. Cassie  |  March 9, 2011 at 9:11 am

    You will probably want a car for the suburb part but really really do not rent a car for the part where you’re in the city. It will cost at least $30 a day to park at whichever hotel you pick downtown. You’re better off with taxis and the el. Bioth are easy (yes, like new york) It’s impossible and expensive to park at any of the places you’ll visit anyway (wrigley, for example). You’ll probably like Millenium Park and the Art Institute. Then you can’t go wrong with any of the other major museums (Field Museum, Shedd Aquarium, Adler Plenetarium or Museum of Science and Industry) Lots of people visit the Magnificent Mile for shopping etc but as a resident I think it’s like a big, cold, crowded mall with traffic. And expensive sales tax . ;-) The new glass boxes on top of the sears tower are cool if the weather is clear. Or you can go have a drink at the bar in the hancock bldg and avoid paying the expensive entry fee but still get the same nice view. As for food it kind of depends on what you like. And which hotel you end up at. Let me know if you want more specifics.

  • 6. Katy Livingston  |  March 9, 2011 at 9:16 am

    Hey there, my husband is from Chicago! I’ll ask him and get back to you, but I would definitely rent a car if you’re going out to the suburbs. In the city, parking is uber-expensive, but you could take the L or cabs… But if I went, I would definitely want to go to the Sears tower with the glass bottom. It looks awesome.

  • 7. Bec  |  March 9, 2011 at 9:55 am

    A general question…Are you taking Jensen with you? If you don’t rent a car, how do you travel with babies in taxis? Taxi Cabs don’t have car seats do they?
    (Yes, I am sheltered and live in a really small town!)

  • 8. angelica  |  March 9, 2011 at 10:12 am

    i loved chicago! while your in the city you really don’t need a car- there are trains, taxis, etc. millenium park and navy pier are must sees, and the architectural tour via water is pretty fun too. there is a lot of shopping, and tons of museums.. and pizza. you must eat at gino’s east. its the best! it will be warm (i went in December in the middle of a blizzard) so you can go to the lake- there is a beach and an amazing beach bar thats always featured on the travel channel for being one of the best beach bars in the US!

  • 9. Ashley  |  March 9, 2011 at 10:24 am

    Chicago is an awesome place to visit. I was there this past summer and it was a blast. If I were you though, I dont think I would necessarily rent a car because it is kind of like NYC with everyone walking around. No one really drives cars, unless they are taxi’s and from the few days I was there, I never really saw places that you could park.

    Navy Pier is a blast. It seemed to me like it was more for younger kids, but it is fun to walk around and see the water. Oh and make sure that you have their pizza, its nothing like texas bbq but its still really good :)

  • 10. The Stephanie  |  March 9, 2011 at 10:34 am

    Only been a few times for a conference, but here are my thoughts:

    You must eat at Gino’s East (pizza). If you stay at Navy Pier, you shouldn’t need a car, you can walk everywhere. You should definitely got to Navy Pier.

    I know, I’m just tons of help, right? :)

  • 11. Nora  |  March 9, 2011 at 10:53 am

    Oo, fun! I’m going to a wedding in the burbs this summer too. In August. I don’t suppose it’s the same one.. that would be too bizarre (but also supremely awesome). And side note, depending on when you’re there, if you have any free time at all to meet a fellow blogger let me know cause, um, I’ll be up in that region soon. Anyway, I have nothing to offer in terms of what to do/where to go because I’m more excited about you being close to where I live :) But I will say that Wrigley is worth even as a diehard StL Cardinals fan. And the hot dogs there are unlike any other ballpark hot dog. True Story.

  • 12. Stacie  |  March 9, 2011 at 11:12 am

    My recommendation is always: go to Ed Debevic’s. It’s a little diner where the staff treats you like dirt! On purpose though, so it’s super funny. On my way to the bathroom one waitress yelled at me, “Make sure you remember to WASH your HANDS.” And then our waitor stole my friend’s sunglasses!

  • 13. Lesley  |  March 9, 2011 at 11:49 am

    You do not need a car while in the city. You will get too frustrated trying to find a place to park and parking will be big bucks! I also recommend the architectural boat tour. We had a blast on that our tour guide was Bacari (like the run Bacardi but without one letter – that is the only reason I remember) Wrigley is Awesome! We were only in the city for 2 nights and stayed at Best Western Hawthorne Terrace. It is not fancy but it was clean, reasonably priced and a nice walk to Wrigley. We grabbed some beers before the game at Goose Island near the ballpark, then ate junk food for dinner at the game one night and at the Weber Grill restaurant another night. Very neat and the food was great but I am sure there are so many other great choices as well. We wanted to stay longer just to try more restaurants. Magnificent Mile is nice to walk if the weather is good but as for shopping I could care less and would skip it if you don’t have time. Navy Pier was nice and this is where we got the boat tour.

  • 14. Priscilla  |  March 9, 2011 at 5:06 pm

    I was going to mention that you might want to check to see if there are any festivals going on while you are there. Someone already mentioned Taste of Chicago. That one is divine!

  • 15. Debbie  |  March 9, 2011 at 5:11 pm

    I’ve never been to Chicago so I definitely don’t have anything important to contribute to this post. I would just add that I hope that you find a great pizza place to eat some deep dish pizza while you’re in town. Everytime a friend goes or comes back from there I drool over their pics of pizza. Ha, can you tell I’m hungry? Sorry for being zero help whatsoever. Excited that you’ll get some time away in a new city. I’m sure you and Stephen will enjoy the time together. Have fun! :)

  • 16. Jen  |  March 9, 2011 at 5:36 pm

    Here are my thoughts…call Brad, I would not rent a car until you go to the burbs, and get the stuffed pizza and chicago hot dog oh and the Italian Ice…yumo!…this will be one of the topics we can chat more about when I see you next! :)

  • 17. april  |  March 9, 2011 at 7:19 pm

    I second Gino’s East – that pizza was head and shoulders above the other Chicago pizzas … just give yourself more than enough time to eat (45 minutes for a deep dish to cook) and order something to eat for an appetizer so you’re not sitting at your table staring at everyone else’s food for an hour.

  • 18. Rachel  |  March 10, 2011 at 12:06 am

    Call Brad… That’s my best advice. :)

  • 19. Kyria  |  March 10, 2011 at 8:24 am

    You definitely don’t need a car in the city. I suggest Lakeshore drive as well! If you like natural history, you have to go to the Fields Museum! Also the Bean is really cool and just walking around downtown is great.

    When you are in Wrigleyville, you should stop at — Guthries! It is walking distance from the stadium and has games, all kinds of board games! It is so fun!

  • 20. Kristin  |  March 10, 2011 at 10:15 pm

    I’m too lazy to read all these comments, so sorry in advance if this is repeat but:

    You could get away with out renting a car while you are in the actual city (but you’ll probably need one in the burbs) and you’ll be happy to not have a car- parking sucks and is uber expensive by Wrigley. Taxi’s are plentiful, plus there is the subway/train and other forms of mass transportation- not glamorous but convenient.

    The Shedd Aquarium is AWESOME. Michigan Ave. has a great shopping/food district. Gino’s East is amazing pizza. The building formerly known as the Sear’s Tower (what’s it’s new name?) is cool if you are not afraid of heights. If you are into art, the museum at the Chicago Art Institute is so wonderful and amazing. Navi Pier in the summer is fun. I’m pretty sure there are some cool bars in the Wrigley district if you are into that.

    If Taste of Chicago is going on while you’re there, go. It’s delicious and one of the best food fests, I’ve heard.

    This is a lot, but if you need anymore suggestions, hit me up. I’ve lived in Milwaukee my whole life, so I’ve been to Chi-town a lot.

    PS- I think it’s awesome that you are not a Cubs fan!

  • 21. Kristin  |  March 10, 2011 at 10:19 pm

    Oh- I forgot: The Museum of Science and Industry is really neat too. So is the Field Museum (I really love museums…). There is a park, I think it might be Millennium (or Millennial) Park, that has this big silver bean shaped sculpture that is cool to take pictures in front of.

  • 22. Kathryn  |  March 11, 2011 at 1:09 pm

    Taking the train from Midway is super easy, and cheap! You can get right into downtown no problem!
    Make sure you go to the Millennium park to check out “the bean” and enjoy shopping on Michigan Ave! I don’t like deep dish pizza, but that’s just me, my husband couldn’t get enough of it!

  • 23. Diana  |  March 11, 2011 at 3:46 pm

    If you want to splurge, like jazz music and have an AMAZING steak dinner go to Sullivan’s! So great! Also, staying anywhere between Michigan Ave (the Mile) and the museums will pretty much ensure that you’re in the middle of things. You can get some great deals (someone mentioned the Knickerbocker) just off the mile. Public transport is def the way to go in the city-but you WILL need a car for the suburbs. Lastly, there’s a place called FoodLife in the water tower (end of Michigan, where Macy’s is) that’s like an upscale cafeteria, fun and great for brunch. You get a card and they swipe it for you, then you pay when you’re finished eating.

  • 24. Erin  |  March 13, 2011 at 10:21 am

    You are coming to Chicago??? I happen to know a really awesome twin mama who lives in the suburbs. ;)

    The Frank Lloyd Wright Home and Studio is just outside the city in Oak Park. It’s an awesome tour if you like looking at cool houses.

  • 25. Becky  |  March 13, 2011 at 12:36 pm

    There is an archeticture boat tour that is really cool! I’ve been to chicago 3 times and went on it all 3 times! The museums are all really neat and fun! The first time we went we did the mob tour-It was pretty cool! They have a Dick’s Last Resort, which is a lot of fun, if you are into being ridiculed. Navy Pier-depending on when you go in the summer there is a chance for fireworks…which are neat!
    Have fun!

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