Although I may be slightly biased (having been born and raised in Chicago), I truly believe Chicago is the greatest city in the world. Where else can you find 26 miles of stunning, public beaches on a gorgeous lake, world-class museums and restaurants, fascinating history, and awe-inspiring architecture? Not to mention the friendliest locals you'll ever encounter in a major city.
As someone who has travelled extensively myself, I know how confusing/time-consuming it can be to consolidate all the info out there prior to travelling, so I thought it might be helpful to share some thoughts/advice from a native Chicagoan. All these tidbits are purely opinion-based, but I've written what I would want to know if I were visiting here from out of town.
1. If I could only advise you on one must-do activity while you are here, it is hands-down the boat tour run by the Chicago Architectural Foundation. While there are many other boat tours in town that are decent (I've done Wendella, Sea Dog, etc.), none even compare to this. Unlike the others who often hire unenthusiastic young people to memorize scripts, CAF's tour is guided by experts in their field who are extremely knowledgable and you will get the best tour of Chicago you could possibly ask for. Recommended for all ages. Im 29 and my husband and I love it, and it is such an enjoyable experience, my parents continue to go at least once a year. Definite must.
For some "classic" Chicago fare, head to Portillo's on Ontario St. or The Berghoff (est. in 1890s!) on Adams St. for lunch, or Uno's/Due's for dinner. Uno's and it's twin-sister Due get jam-packed with heavy wait times, so take that into account, especially if you're going on a Fri or Sat. If you want a great view of the city with a hip and upscale (but not snooty) vibe, go to Fulton's On The River for lunch or dinner. They have fantastic outdoor seating. The best restaurant view of the skyline is at the Signature Room on the 95th floor of the Hancock building. Absolutely stunning. Insider's tip: Signature Room is a tad pricy, so one thrifty way to still get the great view/experience is to head one floor up from the Signature Room, to the Signature Lounge, where there is a bar and you can grab a cocktail and take in the skyline. The drinks are still pricy, but it is worth it for the view, and it still beats a full dinner tab! Of course the list of incredible restaurants goes on, and there are many more that are worth visiting, but those are a few I'd recommend.
Best ground-zero view of the city/skyline is outside the Adler Planetarium. You will get your greatest photo ops here (and it's free!), so don't forget your camera.
They are phenomenal, and you really can't go wrong with any of them. My personal favorites are the Art Institute and Science and Industry, but Shedd Aquarium, Field Museum (natural history) and Planetarium are also top-notch. Best museum for kids is definitely Science and Industry....they have tons of exciting exhibits for children, including real baby chicks that you watch in various states of hatching, a simulated coal mine that you actually go underground in a train car to experience, and perhaps the world's largest, most elaborate (and most expensive) doll house that you have to see to believe.
Despite what you may have heard, Lake Michigan is 100% safe to swim, and I've grown up doing so! North Ave. Beach has a party atmosphere during the day on weekends (and even has a rooftop bar on the beach house, so if that's what you're looking for, you'll have a blast. Montrose and Foster Beaches are more family-friendly, although it's worth mentioning that all of the Chicago beaches have been inviting more unsavory characters in the last couple years. I've never had a problem, but I wouldn't leave anything valuable unattended.
It is most convenient and advisable to get a hotel in the Loop, Gold Coast, Mag Mile, or River North neighborhood, as this is probably where you'll spend most or all of your time. During the day, you can walk everywhere you will want to go, or hop on a bus or "el" train. Make sure you actually check the address of a hotel before booking it, because a lot of hotels claim to be "close to downtown," when in fact, they are not. Don't book a hotel near O'Hare if you plan on spending multiple days sightseeing without a car rental. A cab from O'Hare to downtown is too pricy to be doing every day, and the "el" train ride on the blue line, while doable, takes forever to get downtown from O'Hare, and vice-versa. Also note that parking garage fees in the city are expensive...expect to pay somewhere around $25 for the day/evening. If you are lucky enough to find a spot on the street, it will be relatively cheaper, but you still have to pay and the spot will be time-limited. Look for a nearby pay stand, use your credit card, and a receipt will print out that you put on your dashboard. Make sure you check the time it expires..the meter maids are on their game and you will get ticketed if you go past your time! In terms of riding busses and the el, you can buy a CTA (Chicago Transportation Authority) card in any el station, and this will work on the busses and el. Also look into purchasing a one, three, or seven-day CTA unlimited pass at: transitchicago.com/travel_information/fares/…
Cabs are plentiful in the downtown areas, so this is always a good option, as well.
(Disclaimer: this section is not meant to deter anyone from visiting, it is meant to be helpful. For those who stay in safe neighborhoods, are aware of their surroundings, and follow basic safety precautions, Chicago is an incredibly safe city!)
-The River North, Gold Coast, Mag Mile, and Downtown/Loop neighborhoods are very safe overall. Note that the loop gets somewhat deserted in the evening. Other safe neighborhoods to visit are Lakeview, Lincoln Park, Wrigleyville, Southport, Roscoe Village, Old Town, and Wicker Park. Wicker Park/Bucktown is an eclectic, trendy area with great restaurants and bars, but it is on the fringe of some not-so-great areas (like Humboldt Park and Logan Square), so while it's relatively safe, there are still some rough patches. You can walk and take public transportation around all these areas during the day. At night, it's best to take a cab everywhere, or if you absolutely must walk, walk in a group. Regardless of what neighborhood you're in, I'd honestly avoid busses and the el train completely at night.
-Neighborhoods to AVOID:
The entire South and West Sides of Chicago. Nuff said. Don't go west of Damen or south of Soldier Field (where the Chicago Bears play). Some of the most dangerous neighborhoods in the entire country are on Chicago's South and West sides, and include Englewood, Garfield Park, Austin, Bronzeville, and many more.
As in any major city, we have our fair share of panhandlers and occasional hecklers. If anyone approaches you and tries to ask you for money, sell something to you, or simply makes you uncomfortable, do not engage them in conversation! Ignore them, don't apologize, and continue walking confidently, and they will typically leave you alone. Recently, there have been multiple strong-arm robberies of people's iPhones in the city, especially on the el. DO NOT HAVE YOUR iPHONE OUT IN PUBLIC HERE! Don't open your purse or wallet in public, and don't leave your purse or phone out on outdoor tables within easy reach of passersby. Just be smart, and you will be fine.
8. Entertainment/Night Life
The Second City improv club always makes for a fun night, and it's where some of the comedic legends-- John Belushi, Mike Meyers, Tina Fey got their start. If you're into the theater, check out Broadway in Chicago (Jersey Boys is a phenomenal show). Chicago Symphony Orchestra is fabulous, and sometimes they even do free shows in Millennium Park. If you're looking for a super-trendy bar with great views of the city (and sometimes even a celeb sighting), head ROOF, on the roof of the Wit Hotel. Cubs games are extremely memorable, and the bars around Wrigley Field get pretty raucous before, during, and after game time.
9. Neighborhoods Overview
~River North: Trendy restaurants patronized by young professionals.
~Gold Coast/Mag Mile: Posh/very upscale stores, restaurants, and hotels. Frequented by a mix of ages but tend to be 30+ and more mature. Area along Michigan Avenue is expensive but also must-see Chicago. Chicago landmarks include the Water Tower, Wrigley Building; beautiful views along the river.
~Loop: Willis Tower (still Sears Tower to me!), Daley Plaza, Grant Park, Millennium Park/the Bean within walking distance. Mostly tourists and white-collar professionals.
~Old Town: Good restaurants and bars. More upscale, trendy atmosphere. Young professionals, ages 25+
~Lincoln Park: Very yuppy neighborhood, affluent. Good restaurants and bars. Younger neighborhood but still more mature than Wrigley. Lincoln Park Zoo is here (and it's free admission).
~Wrigleyville: Overall, the atmosphere here is young, post-college, frat-party. Sports bars everywhere. Lots of fun around Cubs games, late-night turns into amateur hour.
~East Lakeview: includes vibrant Boystown and the Belmont Red Line area can get a bit sketchy. Some good restaurants.
~West Lakeview/Roscoe Village: has lots of families pushing baby strollers and young professionals. Not a ton going on here for tourists, but a nice, quiet area overall.
Again, this is all purely my opinion, but hope it helps! Hope you enjoy your time in the Windy City!