We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

New to Chicago - Some Guidance Would Be Appreciated

Burlington, Ontario
Level Contributor
38 posts
41 reviews
Save Topic
New to Chicago - Some Guidance Would Be Appreciated

My wife and I are planning a trip to Chicago, probably in mid September. Hopefully, the weather at this time of year will be somewhat reasonable. We're from the Toronto area and are assuming that it should be similar, i.e. somewhere between 55- 70 degrees during the day with a reasonable chance of sunshine.

We are both theatre lovers and would like to do a show each night we are in the Windy City after a day of seeing the local sights. We also enjoy a good dinner and plan to do a few good restaurants, e.g. Alinea and Charlie Trotters. After doing some research, it appears that most of the theatres are located in the Loop district (we think.) We are looking for a recommendation for a location for a convenient hotel within walking distance of theatres that is accessible to local transit (we don't plan to rent a car and may cab it late at night.) Any advice would be appreciated. We're not sure if the Loop or Millenium Mile area would be best. Shopping is not really an interest for this trip. Hotel recs would also be appreciated. We're looking for a 4-star as most of our time will be outside of the hotel and we would not really take advantage of everything a 5-star would have to offer. Thanks!

Chicago Cultural Center
Art Galleries, Architectural Buildings
Department Stores
Bloomingdale's Home + Furniture
Architectural Buildings, Department Stores
Level Contributor
8,684 posts
24 reviews
Save Reply
1. Re: New to Chicago - Some Guidance Would Be Appreciated

There are a few downtown but id recommend also checking out Shakespeare at navy pier, Steppenwolf and neighborhood venues. River north is a good place to stay, the loop is deserted pretty early

Destination Expert
for Chicago
Level Contributor
7,262 posts
16 reviews
Save Reply
2. Re: New to Chicago - Some Guidance Would Be Appreciated

I would not say that most of the theatres are located in the Loop. Years ago, that was true, but not now. If you look at www.chicagoplays.com you can pick your favorites, though the listings may not yet be complete for September.

I recommend Court Theatre at the University of Chicago for consistently outstanding work, also Writers Theater in Glencoe. (These are not easy to get to without a car.)

As far as hotels conveniently near the Loop theatres, the Renaissance on Wacker or Hotel Burnham come to mind.

Edited: 08 June 2011, 04:02
3. Re: New to Chicago - Some Guidance Would Be Appreciated

-:- Message from TripAdvisor staff -:-

TripAdvisor staff removed this post because it did not meet TripAdvisor's forum posting guidelines with regards to family-friendly language and/or subject matter. We will remove messages or topics that contain objectionable language and images (avatars or links to pornography), including but not limited to profanity, obscenity, vulgarity, pornographic literature, racial slurs, hate speech, personal insults, hostile comments and threatening language.

To review the TripAdvisor Forums Posting Guidelines, please follow this link: http://www.tripadvisor.com/pages/forums_posting_guidelines.html

We remove posts that do not follow our posting guidelines, and we reserve the right to remove any post for any reason.

Removed on: 14 June 2011, 14:05
Level Contributor
7,373 posts
1 review
Save Reply
4. Re: New to Chicago - Some Guidance Would Be Appreciated

Actually the Glencoe Metra stop is practically across the street from Writers Theatre, which I subscribe to and thoroughly recommend. Would just have to make sure that the inbound schedule is reasonably close to when the play ends.

Website is http://www.metrarail.com

Check the schedule for the Union Pacific North line. This train runs in and out of Ogilvie Station.

Lookingglass just became the third Chicago theatre company to win the Regional Tony Award, they are basically located in one of the old water towers at Michigan and Chicago.

I would also imagine that Million Dollar Quartet will still be going strong at the Apollo in September.

Edited: 08 June 2011, 06:52
Mississauga, ON
Level Contributor
3,187 posts
107 reviews
Save Reply
5. Re: New to Chicago - Some Guidance Would Be Appreciated

tbirdal - Your post is quite disturbing.

We are in the preliminary stages of planning a trip to Chicago (also from Toronto as the OP). We have visited Manhattan several times and never once felt unsafe. Same with Paris, Dublin, etc. We are quite shocked and disturbed by your post.

Other Chicago-ans/ites (not sure which if either it is), can you add to tbirdal's post, hopefully dispelling our doubts?

Level Contributor
4 posts
51 reviews
Save Reply
6. Re: New to Chicago - Some Guidance Would Be Appreciated

If you go during the day you'll be fine, and at night stick near the loop or magnificent mile areas and you'll be fine. I would recommend taking a cab if you have to walk more then a few blocks at night. CPD does a great job of patroling the areas. The attacks appear to be gang related and are not as big of an issue as previous posters make it out to be.

Lansing, Illinois
Level Contributor
151 posts
136 reviews
Save Reply
7. Re: New to Chicago - Some Guidance Would Be Appreciated

September is often our best month for weather. Temperatures are often in the 70s and sometimes 80s and we don't have a lot of all-day rain events. It is usually a very comfortable time of the year. As far as crime, as in every other big U.S. city, just be aware of your surroundings and not make yourself an easy target. Unlike many cities, Chicago's downtown stays very busy after 5pm, so you don't feel isolated when you're out and about in the evening. The city just installed a new mayor and police chief, so I'm sure the downtown crime issue will be a priority for them once they get settled in their positions.

Level Contributor
7,373 posts
1 review
Save Reply
8. Re: New to Chicago - Some Guidance Would Be Appreciated

Chicago is not alone in having an issue with the problem of large groups of teens using social media and text-messaging to gather in one spot and create problems.. Other major metropolitan areas have reported the same problem.

To say that the police have no control of it is certainly an exaggeration. They are aware and have been implementing strategies. They will be very proactive, I am sure.

I took the Red Line home last week at around 10:00 without any issues.

Fish Creek...
Level Contributor
998 posts
67 reviews
Save Reply
9. Re: New to Chicago - Some Guidance Would Be Appreciated

I used to live in the Chicago area and we still travel there to enjoy it, it is a fantastic city. As a tourist (not a business person) you will want to stay in the Magnificent Mile, Streeterville, or River North district, not the Loop. It's a big city, so plan on cabbing to many things.

There are many fine hotels throughout the city, but we always try to stay north of the river, east of LaSalle, south of Division, west of Columbus. Lots to do there. Don't forget Andy's jazz club and Blues Chicago!

Level Contributor
8,231 posts
76 reviews
Save Reply
10. Re: New to Chicago - Some Guidance Would Be Appreciated

Allegro Hotel is in the loop and right in the middle of the "theatre district". And to say the loop shuts down isn't even remotely true. It's not as bustling as the River North area, but it's fine, safe, good. Also, there is a JW Marriott that just opened a couple months ago on Adams Street in the loop. It's very nice. Chicago is a huge theatre town and there are so many outstanding venues, you won't believe it. From the off broadway extravaganzas of the loop, to David Mamet style plays at the Steppenwolf, to much more avante garde theatre at the Chopin--you will be so happy. www.theatreinchicago.com