Chicago Food/ Activities/ Local Places to Travel (non typical)?
There are just a few suggestions off the top of my head. If you are looking for something in particular, types of food or things to do, ask and I'll try to give more suggestions. My answer was too long, so I couldn't post things the list of things to do. Ask again and I will add them.
I haven't eaten at any of the food trucks and don't know anyone who has, but Chicago Magazine had an article in May called "18 Awesome Chicago Food Trucks" that may be helpful:
Navy Pier is a shopping, dining, and entertainment destination. The shops are mostly tourist-type places.
There is a food court with McDonald's, Connie's Pizza (a Chicago favorite with other locations including Westmont), and other casual food places. Bubba Gump Shrimp Co., Capi's Italian Kitchen, and Riva Crab House/Riva Cafe are all good places to eat, depending on what you order. Other restaurants include a Billy Goat Tavern location, Harry Caray's Tavern (not the original which is closer to Wrigley Field), Jimmy Buffet's Margaritaville, and City Porch. Garrett's Popcorn has caramel corn and cheese corn that are both really good.
For entertainment, there is a movie theater (with IMAX), the Chicago Shakespeare Theater, Skyline Stage, amusement rides (Giant Ferris Wheel, Carousel, Old-Fashioned Swing Ride, etc.), miniature golf, and a stained glass art museum (free). You can also take a lake or river cruise for lunch, dinner, cocktails, or just plain sightseeing. The Sea Dog is a speed-boat sightseeing cruise. There are also Segway tours of the city from here. See HotTix below for discounts to the Shakespeare Theater and Skyline Stage shows.
PLACES TO EAT:
Billy Goat Tavern Original at 430 N. Michigan Ave. Lower Level (near Wrigley Building and Tribune Tower) is the restaurant that inspired the Saturday Night Live skit (Cheeseburger, Pepsi - No Coke, Chips - No Fries) with John Belushi, Dan Akroyd, Bill Murray and Loraine Newman.
Giordano's Pizza (multiple locations), my family's favorite deep-dish stuffed pizza.
Pizzeria Uno (29 E. Ohio) and Pizzeria Due (619 N. Wabash), said to be the original Chicago-stype deep-dish pizza
Dell Rhea's Chicken Basket (645 Joliet Road, Willowbrook), famous for fried chicken since the late 1930's or early 1940's. Closed on Mondays. On the old Illinois Route 66, a historical road which goes from Chicago to Santa Monica, California.
White Fence Farm (1375 Joliet Road, Romeoville), another famous fried chicken place, also on historical Route 66.
John Hancock Signature Room at the 95th (in the John Hancock Building) with 360 degree views of the city. Not inexpensivve. Has a dress code (casual, no beachwear for luncj; business casual, no shorts, athletic wear, gym shoes, ripped or torn jeans for dinner).
Original Rainbow Cone (9233 S. Western, Chicago) serves a five-flavor ice cream cone. Get a large plain cone with all 5 flavors.
DaveBuster's (Chicago, Addison, Orland Park) a place to eat, drink, and play video games.
Gameworks (Schaumburg), another place to eat, drink, and play video games.
Chinatown (22nd/Archer and Wentworth Ave.) has many shops and restaurants, including dim sum, Cantonese, and Mandarin. You can also get a Chinese massage. Furama Restaurant, King Wah, Three Happiness, Won Kow, are a few that I've visited.
Greektown (Halsted and Van Buren) has over 20 restaurants. Greek Islands is one of the more popular restaurants.
Chicago's Little Italy (bordered by Eisenhower Expressway, Kennedy Expressway, Roosevelt Road (12th) and Polk Street) is the place for Italian food. The University of Illinois at Chicago and several hospitals are also located here. The old Cook County Hospital was the setting for the TV show ER starring Anthony Edwards and George Clooney.
A progressive dining tour offered on Saturday evenings lets you try 3 restaurants for one meal, each course is at a different restaurant. It includes coach bus transportation, a city tour of sites between restaurants, and gratuities and taxes.