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    Chicago Trip Ideas

    I'm guessing if I really wanted to I could find an old thread with this topic, but I'm lazy. Last year my wife and I's anniversary kind of got lost in the shuffle with a 2 month old son and moving from Waterloo to Des Moines, so we'd like to do something a little bigger this year. The idea of doing a weekend in Chicago was kicked around, since neither of us has ever been. She will assume I have already forgotten this conversation, so I'd like to have something planned out before she brings it up again so I can surprise her. So help me out Fanatics! Where would be a good place to stay (ideally wouldn't want to do a ton of driving in an unfamiliar city)? Any good suggestions for things to do/see that skew more romantic and less touristy?



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    Re: Chicago Trip Ideas

    Go to Mario's Italian ice.



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    Re: Chicago Trip Ideas

    We stayed at a hotel (Marriott, Hilton, Best Western??) downtown within a few blocks of Navy Pier. Don't miss the museums if you've never been (I prefer the History and Art museums myself). Also, we went on a boat tour up the Chicago River, and got a good presentation on the various buildings in the area. Took 1 to 1-1/2 hrs and was very interesting (and they served alcoholic beverages).


    "Just remember, what you choose to do with each day is very important because you are exchanging a day of your life for it" -ET

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    Re: Chicago Trip Ideas

    I am going out to Chicago in June for a weekend and Cubs game. I am staying at the Best Western River North in downtown Chicago. It is in a great location, walking distance to many different restaurants/bars/activities, and parking is free. Remember when you look for hotels in downtown to add on the fee for parking which is at least 25 to 35 dollars a night.



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    Re: Chicago Trip Ideas

    My wife and I do a fun Chicago weekend about every year together. This year, we are going the weekend of Sept 7-8 because we are going to hit up a Bears game (I'm a big fan) along with the Michael Buble concert (United Center). The following are some great options for things to do while in Chicago:

    -Go to a Cubs game (L Train accessible on the North Side of Chicago)
    -Hang around Wrigleyville bars and restaurants (next to Wrigley field)
    -See a Broadway in Chicago Show Broadway In Chicago Show and Theatre Tickets (lots of show options
    -Walk the Magnificent Mile – High end shopping downtown Chicago
    -Go to top of Willis Tower (formerly Sears Tower)
    -Go to a Bears game – near downtown (one of the most expensive tickets to get in the NFL)
    -Shop the Aurora Outlet malls (far west suburb as you come into Chicago)
    -Check out the Shed Aquarium (downtown)
    -Check out the Field Museum (downtown)
    -See a comedy show (lots of different fun venues)

    When we go, we’ve stayed at different places, depending on what we want to do. You can always stay downtown, but hotels are super expensive ($150/night minimum) there and you’ll fork over around $45/day parking on your car. A cheaper option for downtown activities is to get a hotel out by O’Hare ($70 night and up) with easy access to the “L” train to take downtown. The cheapest option is going to be to stay out in the suburbs. With that option, you can always do the park and ride for the “L” train to get downtown ($5 to park).

    Some people are wary of taking the “L” train, but my wife and I love taking it (we are big public transportation fans wherever we go). At night, it can get a little sketchy at places, but during the day, it is a very viable inexpensive option. It is by far the best way to get around downtown and its immediate area.

    One last thing worth noting is that Chicago is loaded with toll roads, so if you plan on driving a lot, plan on forking over a ton of money on tolls. Even just driving into Chicago to get there, you’ll have a pretty decent chance of having to fork over a good chunk of change.


    Last edited by Triggermv; 05-21-2013 at 09:54 AM.

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    Re: Chicago Trip Ideas

    I really enjoyed the Museum of Science and industry.


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    Re: Chicago Trip Ideas

    Also, if you are looking for romantic and low key, you can't go wrong just taking a stroll anywhere along Lake Michigan. Millenium and Grant Park are kind of the staple areas to just walk around downtown. There is lots to see everywhere. I also like oldman's idea of a boat tour of the Chicago River. I've never done that myself, but it sounds like a great idea that my wife and I should do sometime. I know we'd enjoy it.



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    Re: Chicago Trip Ideas

    Go here if you like Seafood/steaks.

    Catch 35 - Chicago Restaurant - Chicago, IL | OpenTable



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    Re: Chicago Trip Ideas

    Ed Debevic's is fun

    Not overly romantic though. Ha



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    Re: Chicago Trip Ideas

    Quote Originally Posted by Triggermv View Post
    One last thing worth noting is that Chicago is loaded with toll roads, so if you plan on driving a lot, plan on forking over a ton of money on tolls. Even just driving into Chicago to get there, youíll have a pretty decent chance of having to fork over a good chunk of change.
    If you're going to be doing a lot of driving in Chicago, you could always pick up an I-Pass. I believe they are available to anyone, and will save you time and money (tolls are 1/2 price with pass vs. cash).

    Tolls and I-PASS - www.illinoistollway.com



  11. #11
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    Re: Chicago Trip Ideas

    Depends on budget a lot. We like Chicago as my son lives there. There are some "touristy things" that don't make you feel dirty. Some romantic things don't cost tons of money. Here are few ideas:

    1) If you are a jazz fan, you need to take in a show at one of the clubs.
    2) Take in the Buckingham Fountain Light Show at night with a nice walk through the park.
    3) Take in the Chicago Shakespeare Theatre
    4) Take long walks (or rent bikes, Segways, or rollerblade) along Lake Michigan
    5) Fun to go high in the Sears Tower (okay Willis for you new to Chicago), but you can get a great view of the lake by going to the bar in the Hancock building the floor below the observatory and you don't have to pay admission. That will be a bit touristy, but dinner is one floor below that with fantastic views (but I didn't say the food would be fantastic). it is spendy enough that it isn't so touristy.
    6) We like to get out on the lake. There are lots of ways to do some, some more touristy than others. You can choose from sailing trips, private speed boat rides, dinner cruises, or even the architectural tour on the river that my wife likes. I think sailing takes longer, but gets you away from the crowds.
    7) Got to give her a day, or at least some time at a spa. My bride found a spa at a little boutique hotel (Dana) she liked, but there are others (Ame, Felix...etc.)
    8) Museums are touristy on weekends, but amazingly not so much so during the week. if you are also trying to watch travel expense, the city passes have different offers that allow you to hop on and off trolleys and buses at your pace and stop at the major attractions. The Art Institute may have more romance factor, and is closer in to the city than the others.

    Have fun!



  12. #12
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    Re: Chicago Trip Ideas

    Could check out Second City for a comedy sketch show in the evening.



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    Re: Chicago Trip Ideas

    Quote Originally Posted by MNCyGuy View Post
    I'm guessing if I really wanted to I could find an old thread with this topic, but I'm lazy. Last year my wife and I's anniversary kind of got lost in the shuffle with a 2 month old son and moving from Waterloo to Des Moines, so we'd like to do something a little bigger this year. The idea of doing a weekend in Chicago was kicked around, since neither of us has ever been. She will assume I have already forgotten this conversation, so I'd like to have something planned out before she brings it up again so I can surprise her. So help me out Fanatics! Where would be a good place to stay (ideally wouldn't want to do a ton of driving in an unfamiliar city)? Any good suggestions for things to do/see that skew more romantic and less touristy?
    Honestly I'd forget staying downtown. Especially if you've already been downtown before. It's dead after 7pm except for restaurants/bars and really lacks any culture that makes Chicago special. I'd stay here https://plus.google.com/105968027029...13/about?hl=en . Very reasonable and you're in the best neighborhood in the city. There are so many great shops, restaurants, bars, etc within a couple block radius. Plus the Lake is a few short blocks to the east. There is basically no crime and multiple L stops to take a cheap train downtown should you decide to do any of the touristy stuff. I've lived in this neighborhood for 8 years and you just can't beat it.



  15. #15
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    Re: Chicago Trip Ideas

    I'll third second city, took an ex-gf there who had no sense of humor and she dug it still. Also the Navy Pier Ferris wheel, ******* love ferris wheels.



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