I grew up in the southwest suburbs and have lived in the city for almost six years. I love eating, so this will be fun!
1) Best Deep Dish Pizza: Lou Malnati's is my favourite. One of their crusts, the "butter crust," pushes them to #1, in my opinion. Tip: The location on Wells St is closest to the hotels/shopping area, and it gets very busy in the summer. I have better luck with the location on State Street in the South Loop. Quick trip from the touristy areas on the red line.
2) Best Coffee. This, I must know. Just give me as many names as possible: Metropolis is, without a doubt, my favourite. Their shop is located near Loyola University, pretty far north in the city. It's a long trip on the train from downtown. If you have a car, the parking in this area is not too bad, at least on Sundays. It's usually a Sunday when I drive up that way. Some places in the city brew Metropolis, but Intelligentsia is the other big local brand, and it's much more popular. They have a shop right downtown. A lot of people love it, but it has never been my favourite. I'll drink it in a restaurant with no complaints, but I have walked right by Intelligentsia on my way to Starbucks or Caribou. Iguana Cafe is a fun European-style cafe in my neighbourhood. Their food is decent, the coffee is excellent. This might sound crazy, but I actually really like the coffee from Cafe Vero, which are the Italian coffee shops in Mariano's grocery stores. Great gelato there, too. And we also have a few Lavazza cafés downtown, also with gelato and good food. Stumptown Coffee is from Portland, but you can get it in Chicago at Little Goat Bread, either on Randolph St or in the French Market.
3) Best Bowl of Pho in Chicago. I'm sure we will have Vietnamese food at least once and I will be craving it after my trip to Mexico: I've actually never had pho, so I can't help here! There's a Vietnamese place downtown called Ban Le. I had a sandwich once and really liked it, but I can't really offer informed opinions. I believe there's a Vietnamese area on Argyle Street, which is on the north side near Metropolis Coffee, if you decide to head up that way.
4) Best Sushi: Sushi House (
www.mysushihouse.com i think) with a few locations in the suburbs is my favourite. Oak Park is accessible from downtown on the green line, and it's the heart of Frank Lloyd Wright architecture. If that interests you, it's worth a trip. Great place to walk around. In the city, I like Kai Sushi on Chicago Ave. Downtown among the shops/hotels, I think Oysy is good. They have one location near the Mag Mile and one in the South Loop. Mirai in Wicker Park is popular, and pricier, if I remember.
5) Best Place to celebrate Fourth of July: The fireworks are at Navy Pier, but I kind of hate Navy Pier. Crowded, overpriced, and touristy. But festive on holidays. The lakefront path stretches all along the lake, so there are probably many places where you can have a festive atmosphere with slightly less crowds. Maybe Lincoln Park. I haven't been home during Fourth of July week in years.
6) Best hot dog joint: I don't eat hot dogs, but Portillo's is a huge chain that's classic Chicago. They have other food, too, and some have a pasta place in the same location (just another counter). Hot Doug's is also a standard, I know they have one hot dog that involves foie gras. Superdawg is another one I hear about often. In the summer, you can get Chicago dogs all over downtown, though. My family members that like hot dogs would rather buy a hot dog from a street vendor than go anywhere specific.
7) Best Gelato or Ice Cream Shop: As I mentioned in conjunction with coffee, both Lavazza and Cafe Vero have good gelato. Vero has mini cups for only 99 cents. They have a location on Randolph St, across the street from the north end of Millenium Park. Black Dog (gelato) has crazy flavours, but I haven't tried it yet. For ice cream: Jeni's!!! They are from Ohio and just opened their first location in Chicago last fall. Not cheap, but everything is handmade in small batches, and the flavours are fantastic. They have some interesting ones too, along with seasonal ones. Their Chicago location is in a trendy northside area (Lakeview, or Lakeview-ish, I think).
8) Best Burger Joint: I'm not a traditional burger eater, but Kuma's, Au Cheval, and Paramount Room are all well-known. I don't really know anything about Kuma's besides the name. Au Cheval is on the Randolph St "restaurant row" and it's like French diner food. People talk about getting a fried egg on their burgers at Au Cheval. A friend of mine loves Paramount Room. I know they have a night with a great burger/beer special...maybe Wed night? I like Burger Bar, near the North Ave red line stop, because they have a lot of options, and I can easily get something non-beef, and they have cider on tap. My neighbourhood spot is the Jefferson Tap & Grill, and I love their turkey burger. Love the atmosphere there.
9) Best places to run in Chicago: The lakefront path stretches for miles and miles. I don't run, but I hear it gets very congested between Navy Pier & Oak Street Beach. So if you start downtown and really want a serious run, I'd start at Oak Street Beach and run north, or start near Millenium Park and run south. One of my favourite neighbourhoods, Hyde Park, is along the lake, a few miles south of downtown. They have a lovely park at Promontory Point on the lake. The University of Chicago campus is gorgeous, and the Museum of Science & Industry is the only surviving building from the 1893 World's Fair.
10) Right now, Chicago has no Fourth of July running races scheduled, which surprises me given its status as a City. So, for now, I am planning to register for an eight-mile race at some place called Shabbona Lake State Park, located at Southern DeKalb County, about an hour outside Chicago. Anything else of interest in those parts? An outlet mall, perhaps? There's an outlet mall on 88, the highway you'll take to DeKalb. I think it's just west of Aurora. DeKalb is home to Northern Illinois University and it's an average college town. The rest of the area is quite rural.
11) If I wanted to be surrounded by hipsters, where in Chicago should I go? Logan Square. Wicker Park still has some hipster flavour, but it's transitioning into trendy, and apparently Logan Square is the current spot.
Other things:
- Best brunch I've had is at Meli Cafe in Greektown. That location is small, they've opened a larger location on N. Wells St. The service is sometimes cold and awkward, but the menu is huge, and I've loved everything I've ever had there.
- La Fournette is a fantastic French cafe in Old Town. Really authentic. They have a second location now in Lincoln Park. Fresh bread, amazing macarons, good crepes.
- Hoosier Mama Pie Company is amazing. They're west of downtown on Chicago Ave, and also in Evanston (first suburb north of city). The Chicago Ave location is hilariously tiny. It's so narrow that I still walk past it sometimes. Something like three tables. But if you can get a seat, a slice of pie & a cup of coffee is $5, and it's worth it.
- The French Market is a great place to stop for lunch if you're downtown. It's location in kind of the back of the Ogilvie train station, just across the river from the Loop. They have a ton of different counters and a seating area in the back. Good for groups because of all the options. Sandwiches, sushi, Belgian fries, raw vegan, fancy grilled cheese, crepes, goat meat chili, Montreal-style smoked meat, Vietnamese, Mexican, lobster rolls, and more. Plus Lavazza.
keep the recommendations coming!
I know that's the reason why I like it 
