Chicago in October

I need help. As you can see I never post but we’re off to Chicago in October and I have no idea what to do. First, I’m Canadian and have never been plus on a whim I bought really cheap flights on Westjet with no idea what we should do, where should we stay and possibly a day trip. We like good food and well pretty much else as we never get out of our frozen wasteland. Any help appreciated.

Not to be unfriendly—nothing makes me happier than stopping to help a tourist find his way—but still too general a question. Maybe look around the city tourism site and return with more specific inquiries. Otherwise, I’ll send you to the Lizzadro Museum of Lapidary, the National Shrine of St. Jude, and the Rainforest Cafe in a display of smartassery.

With only a half-dozen exceptions, all Chicago hotels are in a small area of downtown and the Near North Side. Hotwire, Priceline, and HotRooms are good ways to find bargains.

I’ll post to keep the thread alive until people with more knowledge come along. Lonelyplanet has a pretty good iphone app for Chicago ($3.99) that you can kind of play around with.

I really like the Hotel Burnham (, but it’s pricey. I’ve also really enjoyed the tours offered by the Chicago Architectural Foundation ( and this last one is cheezy, but fun cheezy, we really enjoyed the food tour at You end up eating and drinking with a bunch of strangers, good time.

How did you anticipate making that day trip? With a rental car?

If you want to get away from touristy areas and get some neighborhood charm, you could go visit Andersonville. The chamber of commerce is really with it, and they semi-regularly have events like dessert crawls or the like. They also have a nice business district with a crap-ton of independently-owned shops and restaurants. Good food up here.

Try Hopleaf, don’t let the front bar fool you, they have dinner seating in the back and amazing food, dessert, and beer.

There’s George’sfor awesome cake and ice cream.

For brunch try Over Easy or M. Henry.

For pub grub, and a bar menu that is an enormous tome, Lady Gregory’s.

For entertainment, you can try the Chicago theatrical institution Too Much Light Makes the Baby Go Blind (30 plays in 60 minutes) at the Neo-Futurists, which has been running continuously for 24 years.

There’s also dozens of places I haven’t had a chance to try yet.

I’ll agree with** Mr Downtown **that it will help if you can give some idea of what sort of things you enjoy, or what your expectations are for this trip. But – without trying to be a smartass – I’ll offer up some of my favorite Chicago experiences.

The Art Institute of Chicago – Sure, other cities have art museums, but this is one not to miss. Wood’s American Gothic? Got it. Seurat’s Sunday Afternoon on the Island of La Grande Jatte? Got it. Monet’s Water Lilies? Got 'em. And *so *much more.

Billy Goat Tavern – The real-life inspiration for John Belushi’s “cheezborger cheezborger” sketches on SNL. Great burgers (if you like 'em greasy!) and a fun atmosphere. There are a bunch of locatons now, but the original is still the only place for me. Go down the steps in front of the Wrigley Building to Lower Michigan and you’re there.

The Second City – These may not be the glory years anymore, but SC is always a fun time no matter what. And you might just see some up-and-coming stars.

I also second the above-mentioned architechture tours. The boat tours are my favorite, and they run through the end of October. I prefer this as a summer activity, but you’re from the Great White North, so I’m sure you can handle a bit of a chill on the water. It’s worth it.

Oh, and here are some previous threads that may interest you. The third one is about pizza. Do not leave Chicago without getting some deep-dish.

I always recommend the Untouchable Tour. It’s kind of cheesy, but a good way to see lots of the city and hear some amusing stories about our gangster past.

Also, if you bought “really cheap flights” I’m guessing you are flying into Midway airport. There are some cheap hotels near there, and you can take the CTA Orange Line to downtown for cheap. You might also look into a CTA three day pass or whatever fits your timetable.

I recommend checking out TimeOut Chicago. It is also available in a weekly print edition.

I took this tour with some out-of-town guests this spring, it was a lot of fun.