Depends on what you are in to... 

If you want quiet, but awesome architecture and generally beautiful streets, go to Bucktown.   

If you want a lot of foot traffic and a shit ton of things to do at night, Wicker Park or Logan Square is ur jam.  

Hyde Park will put you in the south side with a lot of UIC students and a good amount of up and coming live music spots.  

West Loop is the equivalent of the Meatpacking District in NYC. lots of pretty people and the best restaurants in the city. Awesome place to chill 

Uptown has great Asian good, awesome cultural diversity and a solid resto scene as well.  

Lincoln Park, Lakeview, those nabes are nice, but they are also pretty one dimensional. So just know what you are looking for when you get out there.

Hey Jenna! 

Chicago has so many great neighborhoods that all have their own unique feel. I'll give you a run down on my favorites and include a hotel or two - not sure how much you're looking to spend-I always recommend Airbnb if you're looking for a less expensive option in popular 'hoods.

River North is what I would consider the main tourist neighborhood, although there is plenty there that locals love as well! The James Chicago Hotel and Acme Hotel Company Chicago are two great hotels in this area. It's where you'll find every store you can imagine on the Magnificent Mile and in Water Tower Place, as well as some great restaurants like Bavette's Bar and Boeuf, The Purple Pig, Bohemian House, GT Fish & Oyster, Siena Tavern, Lou Malnati's Pizzeria for deep dish, and Portillo's for a classic Chicago hot dog or beef sandwich. Eataly Chicago, what I like to think of as an Italian eating/drinking amusement park for adults, is also there and worth a visit. Visit the The Peninsula Spa for the best pampering Chicago can offer.

Not far from River North is Gold Coast where you'll find some of the higher end shopping (think Barneys New York, Chicago, Christian Louboutin, etc) and more great restaurants near the Viagra Triangle (if that gives you and idea of the feel of this 'hood). I really love Nico Osteria in the gorgeous Thompson Chicago hotel for a special dinner. Public Chicago Hotel is also a great hotel in this area.

Just south of River North you'll find the Chicago Loop-it's mainly the business area that isn't very happening on the weekends, but it's where you'll find most of the broadway shows in Chicago at beautiful old theaters like the Cadillac Palace Theatre and the Oriental Theatre. For great views head to the Willis Tower. Hotel Burnham Chicago  and the JW Marriott Chicago are my hotel recs here.

Just outside the loop are my favorite spots on a nice day, Millennium Park with The Bean (aka The Bean) and Maggie Daley Park, and The Art Institute of Chicago on a not as nice day. Just south in what is considered the South Loop is the Museum Campus where you'll find the Field Museum of Natural History, Shedd Aquarium, and the Adler Planetarium.

The West Loop is where you'll find some of the best restaurants in Chicago along Randolph Street and Fulton Market. I love Avec, Blackbird Restaurant, Girl & the Goat or Little Goat Diner, Green Street Smoked Meats for BBQ, Parlor Pizza Bar for a sports bar atmosphere, high-end food and drinks at Grant Achatz's Next and Aviary. Check out Cowshed Spa at Soho House Chicago for a great pedicure. You could stay in River North or the Loop and get here easily.

Old Town is a little stretch just north of River North. In general it's more of a mature crowd, but the stretch of Wells St. between North Ave. and Division St. is lined with shops as well as bars and patios that are perfect to enjoy on a nice day/night. The Spice House is a cool shop to stop in, they've got just about every spice you can imagine and then some. 

Lincoln Park and Lakeview are to the north, Lincoln Park is generally a younger crowd with lots of bars filled with Depaul students. Hotel Lincoln is a great spot there with a rooftop bar, The J. Parker for fantastic views. On Saturdays the nearby Green City Market is a wonderful farmer's market to peruse, right in front of the free Lincoln Park Zoo. North Beach is probably the most happening beach in the city, with the partying centering around Castaways.

Lakeview is where you'll find Wrigleyville, home of Wrigley Field and The Chicago Cubs. Wrigleyville is one big party....Clark St. near the field is lined with bars that are packed on the weekends. For more info on restaurants and other finds in Lakeview, you can read more on my blog post here.

My current favorite neighborhood is Wicker Park to the west. There are tons of great bars, restaurants and shopping around the Milwaukee/Damen/North Ave. intersection, as well as on Division St. west of Milwaukee Ave. It's super easy to get to from O'hare as you just take the Blue Line to the Damen stop. Hotels here will be much smaller, Wicker Park Inn is a good choice-but I bet you could find some great Airbnb rentals here. Big Star is one of Chicago's most happening patios, with great tacos and margaritas to go along. Piece Pizzeria and Brewery is not far and has great beers and pizza. 

If you settle on a neighborhood let me know and I'd be happy to share more recs!

I lived in Chicago for 8 years and my favorite neighborhoods are Old Town, River North, Wicker Park, and Logan Square.

As a first timer, I'd recommend you stay in River North.

I like River North because it gives you the option to walk to places like The Bean to see the "bean", pop into the The Art Institute of Chicago, or even head up to the top of the Willis Tower for a view 103 floors up. 

You can also easily walk to Michigan Avenue (fairly touristy with mainstream shops), and end up in the Gold Coast for a drink or meal at the classic Tavern on Rush located in the Viagra triangle (yes, this is what it is called) where there's a good chance you'll also spot a celebrity.

While in the Gold Coast, take a walk to Oak Street Beach to take in beautiful views of Lake Michigan and the city. One of my favorite things to do with my pup.

You'll also find many amazing restaurants in this area! Some of my favorites are:

GT Fish & Oyster - get the oysters for obvious reasons. Sit at the boomerang table if you don't have reservations--it's fun! 

Hub 51 - for the pulled chicken nachos. It's also great because they have everything from sushi to burgers to nachos so great for many cravings at once! The Three Green Bites are one of my favorites too.

Gilt Bar - you really can't go wrong. If you are adventurous, try some bone marrow. And the cocktails they mix are some of the best.

Momotaro - some of the freshest fish I've had. Everything about this place is just great and worth the splurge.

My favorite budget hotels are:

Hotel Palomar Chicago. You can't beat the location, and price for what you get. Plus, Sable Kitchen & Bar is downstairs and a great choice for food and drinks.

Courtyard Chicago Downtown/Magnificent Mile - great location with everything you need (clean rooms) at a good price. 

Four Points by Sheraton Chicago Downtown/Magnificent Mile - another good, clean place with great location.

For splurge hotels, go with:

The James Chicago Hotel - ever since I saw Adam Levine here I kinda just have a crush on this hotel. This place is just trendy. My sister stays here for work a lot, so I've seen the rooms and they are really clean and nice.

Ritz-Carlton Chicago (A Four Seasons Hotel) - I love their outdoor bar and the food is delicious. Location is closer to the Gold Coast, but it's literally steps from Michigan Avenue and a lot of action. Service is the best in town.

The Peninsula Chicago - the spa here is pretty epic and the rooms are really high tech and cool. This is Jennifer Aniston's choice when she's in town.

Hope this helps, have fun!

Have a look at Old Town, Lincoln Park, Hyde Park, Wicker Park,Bucktown, Chinatown Chicago(not really comparable to the larger ones in San Francisco etc but really close to downtown), and Gold Coast to get yourself started. 

Pullman, just in the news because it was made a national monument, is really interesting but depending how long you're staying it could be a stretch to find time to get out there and explore. I'd just caution to be careful when looking west or south, some of the areas can be rather rough.