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First trip to Chicago - Advice on Itinerary :)

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Vancouver, Canada
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First trip to Chicago - Advice on Itinerary :)

Hi there,

I am coming to Chicago from the 12th - 17th August with a friend (we are both mid-20s girls) and neither of us have visited before. We're going to be staying at the HI Hostel downtown.

I have a few quick questions that I'd really appreciate some input into (I'll just list them below so it's easier):

- What is the weather like at the moment - still super hot? We're coming from Vancouver where it's reasonably mild, so just wondering what sort of clothes we should bring. Would a rain jacket be advisable? Looks like you get some epic thunder storms there - is this mostly at night, or during the day too? Does it cool off in the evenings?

- can you buy a daily pass for the el, how much does it cost and where do you buy it from? just wondering if it's worth buying this if we're likely to be catching the train maybe once or twice a day? can you use this on any other forms of transport?

- We have some loose ideas about things we want to do, but wondering if you can supplement our itinerary:

- Planning on going to a White Sox game (would have loved to go to Wrigley Field but Cubs are away that week, I believe),

- to Afternoon tea at the Drake Hotel,

- some sort of cruise on the lake (can anyone recommend any particular cruise company?),

- obviously millenium park and to see cloud gate,

- would like to see a show of some sort - have heard that Peter Pan is showing and is very good at the moment? Are there any other 'amazing' shows (theatre) on that we might not have heard about?

- Sears tower or the John Hancock Centre (does anyone recommend one over the other, or are both equally worth seeing?)

- some shopping along millenium mile.

- Navy Pier - is this a worthwhile stop for adults?

- would be interested in seeing some live music - any kind!

So as you can see our interests are pretty varied and we'd love to hear if anyone has any suggestions that might fit with the activities we already have planned. We're both from New Zealand (currently living in Vancouver) so we'd be up for anything that is typically American/Chicagoan :)

Looking forward to hearing any suggestions!

Thanks so much :)

PS our itinerary might sound optimistic - but we're happy to be on the go... Would rather be recovering on someone else's time than taking it easy and not making the most of our trip :)

Vancouver, Canada
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165 posts
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1. Re: First trip to Chicago - Advice on Itinerary :)

Also - are there any great restaurants or bars around, not too expensive, with a view?

Illinois
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for Chicago, Illinois
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2. Re: First trip to Chicago - Advice on Itinerary :)

Current weather - http://www.chicagoweathercenter.com/

CTA pass information - transitchicago.com/fares_gifts/default.aspx - if you plan to take more than two buses and/or trains within a 24 hour period, a pass is a better value than cash fares.

Current theater information - http://www.chicagoplays.com/

No need to see both Sears/Willis and Hancock. IMO - one's enough.

FYI - it's Magnificent Mile - not Millennium Mile -http://www.themagnificentmile.com/

How about getting out of downtown and hitting up some neighborhood spots? explorechicago.org/city/en/supporting_narrat…

www.chicagoreader.com and www.chicagomag.com for dining and entertainment information.

Vancouver, Canada
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3. Re: First trip to Chicago - Advice on Itinerary :)

Sorry - I did know it was the mag mile but just was thinking about millennium park at the same time.. oops!

just had a quick look at that theatre page and looks great - think we're going to see Peter Pan unless something else catches our eye since it's being performed in such a novel format!

We'd definitely be keen to hit up some local hotspots particularly for interesting shops or restaurants. Would also be keen to hear any recommendations for good Blues?

Thanks again!

chicago
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4. Re: First trip to Chicago - Advice on Itinerary :)

Consider cirque ovo, tickets are half price at travelzoo.com, Peter pan is buy one get one free

Do the Caf architecture tour

Illinois
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for Chicago, Illinois
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5. Re: First trip to Chicago - Advice on Itinerary :)

Downtown blues options:

http://www.buddyguy.com/

http://www.bluechicago.com/

Take a cab to - http://www.rosaslounge.com/

Chicago
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6. Re: First trip to Chicago - Advice on Itinerary :)

Any of the lake cruise options are fine. There is the Mystic, Oddessey, etc. For bars/restaurants with a view- you can go to the Signature Lounge at the Hancock and purchase a drink instead of going up to the viewing area above (be sure to visit the women's bathroom- best view!). There are tons of restaurants/bars on the Chicago river, also the 16th floor of the Trump has a bar, as well as the CityScape bar at the Merchandise Mart Holiday Inn. Hope this helps!

Illinois
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7. Re: First trip to Chicago - Advice on Itinerary :)

Mystic & Odyssey cruises mentioned above are dinner cruises. IMO pricey and not worth the money. Consider a lake/river cruise from http://www.wendellaboats.com/

Chicago, Illinois
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8. Re: First trip to Chicago - Advice on Itinerary :)

As Dave said, you should get out to a neighborhood while you are here. In particular, I think you'd enjoy Wicker Park/Bucktown. Take the Blue Line L train to the Damen stop -- Violet Hour for crafted cocktails is just south of the L stop, also Big Star, where you can hang out on the patio and have tacos. Depending on your tastes in music, the Double Door club might be an option -- it's also right at the Damen L stop.

Or a few blocks north (Bucktown neighborhood), try the Map Room for an extensive beer selection, or go to Hot Chocolate for fabulous desserts. Lots of shops in Wicker Park and Bucktown, too.

South Florida...
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9. Re: First trip to Chicago - Advice on Itinerary :)

We are here now. The temp is mild for folks from Miami! Definitely plan for rain. We are going to Second City and West Side Story. Will report back on those.

Vancouver, Canada
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10. Re: First trip to Chicago - Advice on Itinerary :)

Hi everyone,

Thanks so much for your suggestions. Dave - I appreciate the suggestion of Wendella tours - that sounds more along the lines of what we were looking for, rather than a meal cruise. Would this be better to do in the morning when the sun is (I presume) shining from the east onto the city, rather than in the afternoon when it's sitting behind the city? Thought it might be better for photos in the morning?

Also, does anyone know of any discount coupons for any of the attractions around town, like the Sears tower? If we go up to the restaurant in the Hancock building, would we get a free ride up as long as we purchased drinks?

Great suggestions, Amata, thanks! Might just have to try out Hot Chocolate..!