I was lucky enough to win flights to Chicago.
I will be staying for two weeks commencing 26th August
I have read about all the places to visit and things to do.
I would like to take a train or bus out of the city and stay over somewhere for a day or two
any ideas please
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Chicago in August/September
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Trip Ideas
Do you want another City or someplace just to relax? Take Amtrak to Milwaukee maybe? This is too broad of a question. What are you looking for?
I would just like to see as much as possible as I am in Chicago for two weeks.I thought maybe I might get fed up with the city so go off somewhere a bit more relaxed. I would just like to jump on a bus or train and maybe stay over night elsewhere.I am not fussy maybe even a small town somewhere within a few hours of Chicago. Is Milwaukee nice to visit , I may take up you suggestion
Thanks
Milwaukee is a great idea and I really like it there. It's a nice break from the city if you that is what you are looking for.
However, I urge you to look on this site and others for Chicago neighborhood info. You could spend more than 2 weeks just exploring the neighborhoods. Sure, do the touristy stuff downtown, but then dedicate a good chunk of time to the neighborhoods. There is a ton of info out there you can check out. Many of them are very relaxing and have a lot of park space. For actual activities that I would find relaxing, check out the Garfield Park or Lincoln Park conservatories, the beach, rent a bike and go biking on the lake front path just to name a few ideas.
Oak Park is a nearby suburb that has many architectually significant homes from Frank Lloyd Wright and others. It's the home of FLW and you can find tours. I find it a beautiful and relaxing suburb. You can take the blue line el to Oak Park.
You can venture further north via Metra Train, visit the north shore...specifically Glencoe has the Chicago Botanical Gardens. Ravinia is an outdoor music venue up that way you can check into as well.
These are just some ideas. I'm sure others will have a whole new batch of ideas.
If you’re planning a trip to Chicago, it’s worth looking into staying at Hotel Arista (http://www.hotelarista.com) in Naperville. Even though it’s about 30 miles west of downtown Chicago, Hotel Arista offers by far better accommodations for its price range. For the price it takes to stay in a 2-star downtown you can stay in a l4-diamond hotel that really isn’t that far away at all. However, if you want to be downtown for your time in Chicago, it's still worth staying in Naperville for a day or two; it's quite a nice town.
Thanks Gina
for all your help I was a bit concerned because the travel agent asked why I was spending two weeks in Chicago.
I am so looking forward to it. I am just about to book for Tommy Guns Garage for one of the nights. I have read a lot of reviews and most seem to be good. Any ideas on other things to do in the night.Not forgetting my daughter is only 17 so not able to drink. I would also like to go to a ball game and maybe a show.
fancythat, you registered for this site in June 2009 for the purpose of suggesting a Chicago visitor stay in Naperville?
Please read the rules -- advertising is not permitted!!
If you want to go to a Cubs game, the tickets are probably sold out. Try stubhub.com or craigslist.com for tickets. Or go to a White Sox game.
Thanks tchoiniere
You do not want to stay in Aurora if you're visiting Chicago. While it may be only 30 miles away, the trip is approximately an hour by train and longer if you're driving during rush hour.
Part of the city is staying in the central city to experience the hustle and bustle. Gina has given some good ideas for activities.
In addition to the big museums such as The Art Institute, Field Museum and Museum of Science & Industry, there are lots of smaller ones throughout the area. Gina mentioned the Frank Lloyd Wright area in Oak Park. The Chicago History Museum contains the city's first "L" car and lots of info on the Great Fire and gangster era. The Oriental Institute on the Univ of Chicago campus has a superb collection of middle and near eastern art and sculpture.
Everyone shops on Michigan Avenue, but you can hit some of the other areas of the city. Oak Street between Michigan and Rush is home to exclusive boutiques such as Hermes, Prada, Halston and Barney's New York. Even if you can't buy anything, it's fun to look. You could also head to the area around Armitage and Halsted.
The ace I always keep up my sleeve for visitors is the Baha'i Temple in Wilmette. The gardens are fantastic in the summer and views of the lake are great. You can reach it via the CTA Purple Line and also stop in downtown Evanston for more shopping or a stroll through the Northwestern University campus. Just west of Evanston, in nearby Skokie, is the new Holocaust Museum which was dedicated by former President Clinton earlier this year.
There are a number of free activities you could take advantage of. The Cultural Center and Harold Washington Library have regularly scheduled free concerts. The Park District sponsors free movies in Grant park and Lincoln Park. You can bring a blanket and picnic and watch movies ranging from The Philadelphia Story to Kung Fu Panda.
If you want to see a play, Jersey Boys is at the Bank of America Theatre. The Chicago Shakespeare Theatre is presenting Aladdin based on the Disney movie. There's Blue Man Group at the Briar Street Theatre and Second City. For a complete listing with available discounts, check www.chicagoplays.com.
ebonrub: I might suggest you e-mail katie at forums@fodors.com and ask her to remove the trip report tag.
Just under 1.5 hour train trip from downtown Chicago to New Buffalo, MI., at $18 R/T for adults, will put you in a beautiful, relaxing, quaint, little beach town on the other side of Lake Michigan. Beautiful beaches, sand dunes, quiet nature walks, wineries, great restaurants, little antique shops, art galleries, sunsets but most important, very relaxing.
www.harborcountry.org
Love everyone's ideas!! Citylghts has an exceptional list. Wow, your travel agent said why Chicago for two weeks? I've lived here my whole life and still have a very long list of things I'd like to do. You can see by how everyone's lists vary and offer a wide selection of excellent ideas. Definitely a lot you can do!
It looks like the baseball game question was answered. You should try to go though, to either field. If you go to Wrigley, but sure to get there early and enjoy the entire neighborhood experience. There are several bars and restaurants in the area. Your daughter can go to the some of the places around there too b/c they are restaurant/bars.
Nightlife with a minor? Check into Second City...I believe they offer an earlier show which is more geared toward families (I could be completely wrong), but it's worth checking into. I went there in HS : ) Jersey Boys as mentioned above is another great option. You might also be able to go to the top of the Hancock at night. It would offer a very pretty city lights view. There are also various free/outdoor concerts - Milennium Park, Lincoln Park zoo and other places like that. They may offer free and/or age-appropriate types of shows or activites for a teen. Good luck!
ebonrub, the thing about this area of the Midwest is that, with the exception of Chicago (and few other areas), you really need a rental car for the different destinations in this section of the country, either getting there or for when you *are* there. IMHO, even in Milwaukee you would need the use of a vehicle; although you have more options there than some other places.
For example, the suggestion about New Buffalo (or Harbor Country), which is a nice area. Yes, you can get to New Buffalo via Amtrak. However, IMHO, you pretty much need a vehicle once you are there. New Buffalo is a very small town without any taxi service and most of it is fairly spread out. Although there are a couple of restaurants on the main drag, the best ones are much further away, where you would need a vehicle.
There is no car rental agency in New Buffalo.
There's only one train to New Buffalo from Chicago daily - its ETA is supposed to be 7:35 p.m. but, frankly, it's often late. And one train coming back from New Buffalo to Chicago daily (ETD 10:06 a.m.). So unless you were planning on spending at least a couple of days there, this wouldn't even be an option - because you have to just turn around the next morning to return, without even exploring the area.
New Buffalo has a few hotels, most of them are located by the I-94 interchange - about 1.5 miles from the Amtrak platform. However, the Harbor Grand Hotel is very close to the Amtrak platform (couple of blocks) and the Marina Grand is a little less than 1/2 mile away, as is the New Buffalo Inn & Spa. Still, you really do need a vehicle in this area.
If you didn't want to get a rental car, the suggestions about making day trips to certain areas are good ones. I concur with the suggestions of the Chicago Botanic Garden and Ravinia. You could take the South Shore and South Bend Railroad (see NICTD's website for their timetable and fares) to the Dune Park station to go to the Indiana Dunes State Park and Indiana Dunes National Lakeshore - mind you, you'll have to do quite a bit of walking. You might even be interested in going out to some of the Chicago suburbs, such as: Arlington for the Arlington Race Track (thoroughbred racing), Brookfield (for the Brookfield Zoo) and/or Oak Park (Frank Lloyd Wright tours).
Evening entertainment: You'll likely spend big bucks going to Jersey Boys or one of the other Broadway-type shows. However, there are many less expensive options. You could take in the Lookingglass Theatre's "Arabian Nights" at the Water Tower Water Works on N. Michigan or Cirque Shanghai's "Bright Spirit" at Navy Pier. "Million Dollar Quartet" is still running until August 30.
Oops! That's Arlington Park Race Track. Sorry I didn't see that before I posted.
And "Million Dollar Quartet is at the Apollo Theatre on N. Lincoln Avenue in the Lincoln Park neighborhood.
BTW, the Chicago Jazz Fest is over the Labor Day weekend (September 4-6). Maybe you'd be interested in going. See the City of Chicago's website for details.
Get advanced tickets for the Harry Potter exhibit at the Museum of Science and Industry, you don't have to be a fan to like the exhibit and the rest of the museum will take the rest of the day. The Ganster Tour would be a fun evening activity with a teenager and Chicago has great theatre too. I think Legally Blond might be there when you are. As far as a baseball game go to the park and find someone selling tickets outside. The closer it gets to game time the better the price, be patient and if you don't mind missing the first inning you might just get someone who will hand you tickets. My teenager loves to walk and shop in downtown Chicago. Lake Geneva is not a far drive and there are indoor water parks in some of the hotels-lots of fun for a maybe two nights. When you go to Navy Pier make sure you see the stained glass exhibit/museum-ask at the info desk. This is free and most visitors never walk through the building with these exquisite glass windows.
Galena is a beautiful historic town on the IL/IA border. You would need a car though - its about 2 hours away.
Do not stay in Naperville. There is no point. Its a suburb.
Did you tell us where you are staying? Have you thought about an apartment. You could look on VRBO.com. It might be cheaper and more fun. If you want to do that, post back and we can offer suggestions on location etc. Another poster did that from this site and they were really satisfied with it.
Also - go to Metromix. Its a website that will show you events, festivals, restaurants, etc etc.
A lot of great suggestions. DO take a boat ride out on to Lake Michigan at sunset. You will have the most unforgettable views of the city as the sun goes down behind it and the moon rises in the East. Just beautiful.
Northwestern Campus is beautiful, you can bus it. Lincoln Park is great neighborhood, zoo is free. Good luck on the Cubs tickets. Wrigley Field is a must-see!
Ravinia is excellent idea- take a blanket and pick up some munchies to enjoy a concert on the lawn: http://www.ravinia.org/
Chicago Historical Society can help guide you to the neighborhoods you might find interesting:
http://www.chicagohistory.org/
You will find so much to do, and love Chicago so much, that despite two weeks, you will be very sorry to leave and will be planning your return trip before you leave O'Hare!
Where are you coming from?
Thank you all for some great ideas. It doesn't look like I will have time to go out of the city, if I take up all your ideas lol. I am staying in the Essex Inn. The reviews aren't great but it does have a pool, my daughter is pleased about.
I am coming from Liverpool England. I have said before if anyone ever needs any help getting around the north west of England,don't hesitate to contact me. I owe it to you after all the help I have received on this site. Thanks again I will look in to all these ideas. Can't wait
I think my brother has sorted tickets for Wrigley field.
So I don't have to worry about them.
I am so glad they are sorted beforehand
Well, now that I know where you're coming from- I'm going to even more strongly suggest that you stay with public transportation. We drive on the "wrong" side of the road, ya know!- better to stick to PT.

Have a safe and wonderful trip, ebonrub. You will LOVE Chicago!
I stayed at the Essex a couple of years ago (so things may have changed, but still). It's fine - not a luxury hotel, but it suited our purposes just fine. The pool is fun, just for novelty of being on the "roof" if nothing else (it's really on the fourth floor, I believe, but nothing above it in that part of the building). A couple of bus lines will take you right up Michigan Avenue. Enjoy your trip!
As the above post says, the Essex is ok, but not great. It's sort of removed from most sights and the shopping district. If your reservation there is refundable, you may find a great deal someplace else as many hotels are desperate for business right now. If a pool is high on your priority list, some of the top pools in the city are at the Embassy Suites on Columbus Drive, Intercontinental, Swissotel or Fairmont.
I'm seeing rates between $209 and $256 at the Essex beginning Aug 26. The Swissotel is offering a special rate that ranges between $144 and $192 and the Fairmont is offering $207 per night.
The Intercontinental is offering a pre-paid rate of $177 or $217 with breakfast and the Hyatt Regency on Wacker has a pre-paid rate of $199.
The Embassy Suites on Columbus is offering $159 per night and the Homewood Suites is $149. The Homewoood would give you a full kitchen in your room and includes breakfast and has a pool.
Oh how wonderful you people are wish I could meet you all.
If any of you fancy a trip to Liverpool I will definately give you all the tips you need. In fact I wouldn't give you tips I would put you up for a few days LOL.
I hope everyone in Chicago is as nice as you guys
Thanks again
Just to say thanks again for all the comments and ideas I was given on this site. I had a fantastic holiday in Chicago what agreat city and the people are lovely. I was asked what I would do for two weeks in a city by a travel agent Hey what do the travel agents know. I done all the site seeing that was to be done. My favourites where the boat trip, Lincoln Park Zoo,and Navy Pier. We went to see the Jersey Boys (fab) Tommy Guns garage (very good) and got tickets for the cubs game, never been to a ball game before but thoroughly enjoyed it. I must just add if you are staying in Chicago for longer than three days try and book a Chicago Greeter. These people do a wonderful service,it's free and they give you some valuable information Oh anyone thinking of going to the observatory tower in the John Hancock building why not try the signature room (96th floor) buffet $18. I think its 11am to 2pm midweek. The views are marvellous All in all a fantastic two weeks in a wondeful city
ebonrub, I'm so happy that you enjoyed your trip to Chicago. It doesn't get all the hype of LA or NY, but it is absolutely a terrific place to visit.

Hope you'll tell all your friends!