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Please Help with a Chicago Itinerary

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Old Sep 7th, 2014, 03:34 PM
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Please Help with a Chicago Itinerary

My husband and I are planning a trip to Chicago and we would appreciate your advice. We will have 2 ½ days to spend there. We are driving but will leave our car at Midway Airport and take the train into downtown. Our hotel will be the Fairfield Inn on 60 West Illinois St. We will take the train, the Orange Line, but where do we get off the train? Then should we take a cab? We should arrive about 1:00 pm, we will leave our luggage at the hotel and then…

These are the things we want to do: the HOHO bus tour, lunch at the Signature Room Chicago 360, visit Millennium Park & see the bean, see the Rookery, take the L - brown line, tour the Robie House. If there was time enough we would see the highlights of the Art Institute and the Field Museum. What should we do and when? Please help us with a itinerary!
Do you know of anything we are leaving out, that is a must see?
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Old Sep 7th, 2014, 04:11 PM
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The Orange. Line terminates at Adams, but you should get off at State and Lake, which is closest to your hotel on Illinois. You can then either get a cab or hoof it up to Illinois, which is five or six long blocks, across the Chciago River.

As for your itinerary ... You have plenty to fill 2 1/2 days. The Robie House is the farthest south, in Hyde Park. While there, I'd include at stop at the Rockefeller Memorial Chapel. If you're interested In the Rookery, you might want to consider walking tour with the Chicago Architecture Foundation (onsouth Michigan Avenue)--they have a "historic skyscrapers" tour (or something like that) that includes the Rookery and several other historic buildings in the Loop. If you're keen on doing it yourself, I'd suggest at least including the ceiling at the Palmer House, the Tiffany dome at the Cultural Center, the mosaics in the Marquette Building, and of course Buckingham Fountain in Grant Park.

There's always Navy Pier, the Skydeck and Ledge at Willis (Sears) Tower, Wrigley Field, a Wendella boat trip on the Chicago River ...

I'd do the HOHO bus tour your first afternoon, where you might see things that spark interest in further investigation. Then you could group Millennium Park with the Loop architectural things and the Art Institute on one day. Brown line and Signature Room and whatever else on a second day.

Have fun!
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Old Sep 7th, 2014, 04:55 PM
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Rather than the Hoho bus I would take one of the Chicago Architecture Foundation tours. The one I took included a visit to the Robie House. I also took their river tour.
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Old Sep 7th, 2014, 08:29 PM
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Your hotel web site lists the Grand Avenue red line station as the nearest stop. So I would probably switch from the Orange Line to a northbound red line (toward Howard) at Roosevelt. For transportation questions, the CTA website is your friend (www.transitchicago.com), and they have a good app to help you get around.

I agree with thursdaysd -- take an architecture cruise instead of the bus. The Art Institute, Field Museum, Millenium Park/Bean are all rather close to each other. I also agree with Purduegrad that the Palmer House, Buckingham Fountain, the Cultural Center are all worth a look. I would also add Macy's on State Street (former Marshall Field's flagship) to the list. And they're all close to Millenium Park and the Art Institute.
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Old Sep 8th, 2014, 02:44 AM
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Last year we took a free visitor's tour to a neighborhood of our choice. You have to ask for a guide in advance of your trip. We had a delightful and knowledgeable long time resident of Chicago and had a great tour. We ended up asking him to join us for lunch (our treat). The program is called Chicago Greeter. Guides are all volunteers.

In addition, our goal was to spend as much time as we wanted at the Art Institute and we arrived in Chicago early in the day. BIG mistake was to walk from our hotel to the Art Institute and get foot sore. We should have taken the bus. One of the things we did because we were so tired was to take the bus ride along the lake route just to sightsee. Get the all day pass for bus and subway.
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Old Sep 8th, 2014, 06:29 AM
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The river cruise is great...but I took it on a pleasant summer morning. While the boats have seating inside, I can only imagine that it's better to do the tour from the deck of the boat and that the river could be unpleasant in the cold. When is your trip?

We enjoyed the Frank Lloyd Wright tour of his home/studio in Oak Park.

Here's just my two cents about Chicago. For years, most of my visits (which are usually short since I live in central Indiana and we treat Chicago like a weekend getaway) focused on the Art Institute, shopping on the Miracle Mile and generally just sticking to downtown. While I could appreciate, from there, Chicago's rich history and architecture, the city kind of left me kind of cold. I was missing out on some of the charm of it neighborhoods.

So, with our last could of visits, we've made an attempt to branch out a bit. This past trip in July, we spent some time in Old Town and Lincoln Park and really enjoyed it. We mostly just wantered around to look at all the beautiful homes, but we also made it to the Lincoln Zoo and to the park. We had dinner at Balena in Lincoln Park and really enjoyed it. We also at at Rustic House, also in Lincoln Park, but I didn't enjoy it as much.

So, you might consider heading to one of Chicago's neighborhoods for a bit of a walk and/or a meal. I think it'll give you a different perspective on the city.
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Old Sep 8th, 2014, 06:52 AM
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We did the Rookery tour this summer. Reserve in advance. We enjoyed it, but I would only include it if you are a FLW fan and you've "done" some of the better known attractions on previous trips. FWIW, the Fed Reserve is right nearby and has a visitor center/video. (A little dry IMHO). Don't recall if it requires advance reservations. I think the Board of Trade is right there also, but don't know if it is open for visits.

Robie house: check it's hours. I think it is closed on Tues and WEd? If you go all the way out there, the Oriental Museum is basically across the street and was worth a visit, as is the Smart Museum (small art museum) nearby.
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Old Sep 8th, 2014, 07:20 AM
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All of this is good advise. You will have more than enough to fill your 2 1/2 days. If you enjoy a little walk with your luggage, as suggested above take the orange line to State/Lake and then transfer to the Red Line. When you come down the stairs from the orange line there is a stairway to the Red line just across the street. The Red line is under ground. When you get off at Grand your hotel will be just 3 blocks to the east.

The Fairfield is just 2 blocks from my favorite restaurant in Chicago, Volare. The building is very unpretentious but the food is the best Italian I have had in many years.

I would suggest getting the 3 day pass for the Loop and bus. When I was there in January it was $25 for 3 days.
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Old Sep 8th, 2014, 02:09 PM
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Thanks for the advice! I am getting excited about this trip and the main problem will be trying to squeeze everything in to 2 1/2 days!
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Old Sep 8th, 2014, 08:54 PM
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The Orange Line doesn't really terminate except at the airport. It travels around The Loop and Adams is the last stop before it heads back to MDW.

You could save lots of time if you park near your hotel and skip the train. On www.spothero.com, you can find parking at rates comparable to MDW within a couple blocks of your hotel. If you park at the long-term airport lots, you must take a shuttle to the terminal, then walk to the rail station. The Millennium Park garages are around $28/day and around a 15 minute walk to your hotel (about a half-mile).

I'd also recommend someplace besides the Signature Room for lunch. The food is just ok and a bit on the pricey side. Instead, head to the lounge in the early evening. You can watch the sun set over the city, then head elsewhere for a nice dinner. For restaurants, check www.chicagomag.com or www.chicagoreader.com. You can search either by price, cuisine or neighborhood.
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Old Sep 9th, 2014, 04:02 AM
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When are you coming to Chicago? Weekend or weekday?

It's surprising to me that first-time visitors so often have an arm-long list of daytime attractions and little or nothing mentioned about evening and nighttime activities. Wasting 1/3 of the time they are there, IMHO.

Do you have any thoughts in that direction?
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Old Sep 9th, 2014, 05:27 AM
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princess: I assumed that (perhaps erroneously) due to the unique things the OP wants to do, that this wasn't a first trip. If it is, I would certainly suggest sticking with some of the better known attractions (they are better known for a reason!).

Regarding evening/nighttime, we have done guided tours and productions at night, and I like just walking around in a bustling city at night. That said, we are often a bit tired after all we do during the day while in Chicago, so evening activities are not necessarily a top priority (but we aren't big on theater and similar that might be more important to others).
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Old Sep 9th, 2014, 06:23 AM
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We also don't put a whole lot of effort into night time activities for Chicago. I've been to Second City a couple of times and that's fun IMO, but we mostly just plan on a leisurely dinner and, perhaps, an after dinner cocktail. We're not theatre people really and, frankly, I'm usually so exhausted from walking around all day that a long dinner and a relatively early retreat to the hotel are just fine by me. I'm past the point in my life of enjoying "nightlife."
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Old Sep 9th, 2014, 07:50 AM
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Bitter & indyhiker, I hope you don't think I was criticizing your comments. Just making a general observation. And it isn't just applicable to Chicago but other locales as well.

We don't know the ages of the OP and party. I am, too, assuming that these are first-timers because of the way they are phrasing the question. That, and the fact they want to use the HOHO.

Once they mention when they are coming (weekday or weekend - and dates), I could make more applicable suggestions and how they can set up their time to include most of their wish list items. I'm wagering that it will be a long weekend.

Actually, "nightlife" doesn't necessarily meaning bar-hopping, etc. There are a lot of things you can do in the evening and at night. Some of these don't take a great deal of energy and some are for those who haven't worn themselves (yet) with daytime efforts. Just off the top of my head:

Both the Willis Tower and Chicago 360 are open quite late (11 p.m., with last entry 1/2 hour before, I believe)

Second City, iO or another comedy club (SC mentioned above)

Local Chicago-style theatre in the outlying neighborhoods, as well as the Broadway-style theatre most common to those venues in the Loop Theatre District

Jazz or Blues club. Several have different early and late sets. In addition, the Green Mill has their Uptown Poetry Slam on Sunday nights prior to jazz performances.

Some of the other concert venues are not far away (i.e., the Metro, Schubas, etc.)

Old Town School of Folk Music.

Unique Movie Night. The Music Box Theatre on the N. Southport Corridor in the Lakeview neighborhood has some very interesting options, including, upon occasion, silent films (with organ accompaniment). The Landmark Century Cinema on N. Clark, just north of Diversey, in the Lakeview neighborhood shows indies, docs, etc. (This theatre is a stone's throw away from the north end of the Lincoln Park neighborhood, too.) Right in the Loop, across from the Chicago Theatre, the Gene Siskel Film Center.

And, of course, you have dance, opera, symphony options right "downtown". The Harris Theatre, at Millennium Park, is the venue for some of the smaller local troupes and groups, as well as other performers.

Sporting events.

Maybe you just want to go to a little neighborhood bar for enjoying some of those craft beers and ales from the immediate area.

And, if I might suggest - and recommend this - as I have been doing for years: When you go to these choices away from the "downtown" areas (and most of them ARE located away from there), it is an excellent opportunity for you to enjoy some of the wonderful neighborhood dining options - and see what Chicago is all about. Don't confine yourself to only a really teeny-tiny area of Chicago, because you are doing yourself a disservice.

For example, you could go out for dinner/drinks at Wood (on N. Halsted) and a theatrical performance at TimeLine Theatre - both are within blocks of each other. Or go up to the Lincoln Square neighborhood for a dining option and go to a musical concert at the Old Town School of Folk Music.

To the OP: The Chicago Architecture Foundation (a not-for-profit organization who uses docents with much formal training) has their own trolley tours (i.e., "Skyline Vistas by Trolley"). HOHO is a commercial enterprise. The CAF also has tours utilizing the various 'L system to get around ("Must See Chicago") - and you can get comfortable with using the 'L, although you are already coming in on the Orange Line.

One of the above posters is mentioning the Chicago Greeter Service where you reserve in advance and you can customize your own tour. However, with only 2.5 days, you might look into the free Chicago *InstaGreeter* tours of the Loop and Millennium Park, which originate from the Chicago Cultural Center.

Without knowing any more details of your visit, here is what I suggest as a rough outline. Of course, you will be dependent on weather for outdoor activities (such as an architectural river cruise).

First 1/2 day: (If possible) CAF tour of some type. If you don't desire one on the 'L or by trolley, look at their highly-regarded River Cruise. In fact, in light of the buy 1-get-one-free River Cruise offer they provide for members, take a look if the membership option, if you are planning on using them again during your stay - or within a year's time (if you plan on returning).

Chicago Cultural Center (they have a visitor's center as well as free concerts and exhibits - plus a building tour). As mentioned above, the InstaGreeter tours originate here as well.

Millennium Park.

Dinner and/or entertainment option

1st full day:

Breakfast nearby, maybe Toni Patisserie? Corner Bakery (a national chain - but a step above McD's, etc.)?

Art Institute - allow 3-4 hours for **just the highlights**. And STRONGLY recommend that you get the audio tour (small amount extra pp, to help you locate them). If you go at opening, then you'd be through by 1:30 p.m.-ish.

Afternoon, walk through Grant Park (weather permitting) to the Field Museum. If weather doesn't permit, it's just a short cab ride or you could walk over to State (3 blocks west) on Adams and pick up the #146 SB Museum Campus bus.

In the evening, really think about your outlying neighborhood options. Although it might take a little more time to get there, I'm betting you won't regret it.

2nd full day:

You would need to go to the Hyde Park neighborhood for the Robie House. It will take some time to get there, as it is 7 miles south of the Loop. Expect about 35-40 minutes by public transportation - less if you take a cab (although that will cost you). I recommend that you take the #10 MSI (Museum of Science and Industry) bus, IF it is running on the day you wish to go - weekends only this time of year.

While you are down in Hyde Park, why not enjoy some of the other sights? The University of Chicago campus and their museums (the Oriental Institute, Smart Museum of Art, the Renaissance Society); the MSI (is a BIG museum, has a Disney archives exhibit currently running, and (of course) the U505 WWII German Submarine); Jackson Park - and the Garden of the Phoenix - just over the Clarence Darrow Bridge from the MSI.

This is a really full day so think about something closer at hand. Remember the "downtown" options for evening activities I mentioned above.
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Old Sep 9th, 2014, 12:27 PM
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Oh, certainly no offense taken! I'll admit that I run out of steam by nightime, but certainly not everybody does. I really appreciate you taking the time to offer some suggestions. I'm going to file that away for future reference!
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Old Sep 9th, 2014, 01:36 PM
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Don't sell yourself short, indy. You'd be surprised how far you can get with that second wind!

Just so many other activities to consider in the early evening/night besides merely dining - both "downtown" and in the outlying neighborhoods. That's what makes Chicago so great - the sheer number of choices!

Next time you are going up to Chicago, just post an inquiry (including dates) and I'll give you a few options to consider.
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Old Sep 10th, 2014, 12:02 PM
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Thanks again for all the great information! We have decided that we need one more day...so make that 3 1/2 days in Chicago. We are in our early 60's and will probably go out to dinner and go to the hotel! I have considered seeing the Million Dollar Quartet or some musical. We have decided that the Art Institute is a must. We have a grand niece who is a student at Chicago State University and we want to take her out for lunch or dinner. We will be there the last of October.
BTW, it is our first trip to Chicago!
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Old Sep 10th, 2014, 12:07 PM
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Oh, someone asked when we would be there...Monday to Thursday.
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Old Sep 10th, 2014, 01:38 PM
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Thanks, exiledprincess! I'll be sure to take you up on that!
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Old Sep 10th, 2014, 02:03 PM
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I was just in Chicago last weekend and in my opinion the CAF river cruise is a must. I see that you're going the last weekend in October so weather might dictate that. Not sure how fit you are but we also enjoyed biking along the waterfront. If you like architecture a train ride to Oak Park to see Frank Lloyd Wright properties is also worthwhile. Chicago is a great city!
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