Adam's Rough Guide to Chicago for MAX attendees
Getting downtown from the Airport
Save your pennies for beer and take the blue line CTA train from O'Hare or the Orange line from Midway towards towards the loop. At $2 it's far cheaper than your $40 cab ride. Heck, depending on the time of the day it may be faster too.
McCormick Place - the venue
It's located in the south loop area which isn't exactly central or near the fun. If you run at all, it is located right on the lake front path so you can head out North along the 17 mile running path over lunch without hitting traffic.
Getting around
The city has hundreds, maybe thousands of cabs but if you want to save some money, the "El" and the bus network can get you all over the city for $2 per trip. To find your way to a resource below you can use the CTA's tripsweb site.
Touristy Fun Things to do
Rent a Segway for $70 for 2 hours
Chicago River architecture tour 1 hour leaving from Michigan and Wacker
Sears Tower (tallest US building)
Sunset booze cruise
Wrigley Field is at Addison red line el stop. The Cubs are done until maybe the post season but to visit the neighborhood wait until night and skip to the bars section.
Open top / double decker bus tour of Chicago downtown
Touristy things I'm less fond of
Navy pier. Long walk. Lots of tourists, lots of cheezy restaurants and a ferris wheel. Your choice.
Michigan Avenue. Lots more tourists, lots of shops and a few over-priced restaurants. See the section on eating if you are hungry.
Restaurants
Brauhaus - 4732 N Lincoln Ave - Located in the old German neighborhood you can swing steins to the sounds of Polka while you enjoy an authentic bratwurst
Signature Room - Michigan Avenue - On the 95th floor of the John Hancock tower you can watch the sun go down and sip martinis to wash down expensive food with an amazing view
Adobo - 1610 N Wells - Best upscale mexican I've ever had. They prepare Guacamole at the table and I heartily recommend their marguerita with a mescale floater (a smoky taste). Located in a trendy neighbohood with bars nearby.
Parthenon - 314 S Halsted - Greek restaurant with fantastic authentic food (I was in Greece last year so I feel comfortable making that statement)
Bars
South Loop Club - 1 E Balbo - closest to the south loop hotels and host to a good array of locals, TVs and Old Style.
Mullens - 3527 N Clark St - Foosball and good beer specials. Close to the Addison red line el stop.
Fado - 100 W Grand - Irish pub in the styling of many others but showing English Premier League games.
Hopleaf - 5148 N Clark St - Further north but a VAST selection of beers of every style. Located in a neighborhood called Andersonville which is also home to some great restaurants. Probably a taxi ride but worth it for the beer.
Blue Frog - 676 N La Salle Drive - Karaoke on Tuesday, Thursday, Friday and Saturday, board games and a tiny bar. Excellent fun.
Bad Dog Tavern - 4535 N Lincoln Ave - Located in Lincoln Square, an old German neighborhood (See brauhaus). Take the brown line from downtown to Western for $2 or a cab for more like $20
Overall neighborhood notes:
Lincoln Park is home to Chicago's yuppies and plenty of great bars, restaurants and late night dancing if that's your interest.
Wrigleyville is just north of Lincoln Park and home to some of the crazier bars, sports fans and people falling over drunk.
Lincoln Square is a more mature offering (think thirty somethings)
The loop is pretty deserted except for tourists and people attending the theatre after 5pm on weekdays
River North has an upscale feel to all the bars
West Loop has great restaurants and leads into Greek Town - definitely worth a trip
Wicker Park is home to some great music venues and a more "grungey" atmosphere, but slowly become more of a scene
Andersonville is an old Swedish neighborhood and although a little further north it's worth the effort
Rush Street is known as the Vi*gra triangle and is packed with rich men with Harleys trying to pick-up women half their age.