I have two favorite cities in the United States, Chicago (of course) & Miami. I go to Chicago when I need a break from the heat, I want to relax at rooftop bars with unbeatable views, & I want some new trendy finds. Sometimes I'll even catch the city on a good weekend & stumble upon a food festival, special event, or pop-up. I tend to do a lot of shopping in Chicago, probably due to the fact I always stay on The Magnificent Mile. But how can you blame me? Chicago has a beautiful stretch of big box retailers, boutiques, & specialty shops. Check out Water Tower Place first. WTP is my favorite mall on Michigan Ave. Find the wine bar on the bottom level, they have happy hour! Right across the street is 900 North Michigan Shops also a great mall with a gorgeous christmas tree in the center during the holidays. Shopping aside, Chicago is definitely my destination for deep dish pizza, museums, & entertainment. Don't get me wrong, when you want a night on the town, Chicago can offer that too. If you're interested in staying on a rooftop bar for the whole night I recommend I|O Lounge or Cindy's. The Godfrey (I|O Lounge) is northeast of Streeterville & faces the heart of Chicago. Cindy's is near Lake Michigan & has a great view of Millennium Park (including the bean). If the raging bar scene is more your speed El Hefe, Sound-Bar, The Underground Chicago, & Public House are some of my personal favorites. These bars are all within a few blocks of each other which makes it easy to bounce around & see what you like. They all get going around 11 p.m. & you don't want to be fashionably late because unless you're buying a bottle you'll be standing outside for 2 hours waiting to get in. If you're looking for daytime entertainment I recommend The Art Institute of Chicago, Field Museum or Shedd Aquarium. Give yourself at least a day per museum because they are huge & there is so much to see. Chicago offers over 200 theaters so if you're more into the theatrics I'm sure something great is playing. A few years back I snagged a great price for the musical Wicked just being outside the theater at a great time. If getting day drunk is your thing, like it is mine on every vacation I take, check out these breweries: Vice District Brewing, MoodyTongue, & Motor Row Brewery. There are also some noteworthy wineries & cideries all over the city. Now let's talk about the really good stuff, breakfast, lunch, & dinner. My favorite. Check out Kanela Breakfast Club, voted #1 in Chicago, Yolk (Chef Alvaro Gijade @ the River North Location is great), & Eggsperience. For lunch, hot dogs, it's Chicago. The answer to everything is either hot dogs or deep dish. U.B. DOGS & Portillo's will get the job done. If you're really not into meat, Shake Shack, The Chicago Diner, or BAD HUNTER. Moving on to dinner, it really depends on what kind of dining you're going for. My first night in the city I'll always be at Giordano's, it's a Chicago staple & you really can't say you were in Chicago if you don't get deep dish pizza. My second night is always a little more... hmmm.. fine dining? The Signature Room at the 95th is my go to. The drinks, the view, the food, wow. The third night, fourth night, fifth night, it's all up in the air. I try to check out at least 3 or 4 different restaurants because like I mentioned, the city has sooo much to offer. For more suggestions look through these menus: Chicago - Grand Lux Cafe | Menu, Ed Debevic's (might be closed for relocation)| Menu, Quartino Ristorante | Menu, & Green Mill | Menu. Other than food, drinks, & entertainment, here are some other attractions you should consider visiting if you're going to Chicago: Skydeck Chicago (I recommend going toward sunset or nighttime), Chicago River Walk, & Navy Pier (you can find a list of their upcoming events here Events List). All in all, Chicago has something for anyone & everyone. From the rooftop bars to the underground clubs, from the art district to Chinatown, & eveywhere inbetween, Chicago is my favorite city to get lost in. I hope you enjoy my recomendations, maybe use some of my suggestions & go explore Chicago!
For my most recent trip, just like all of my vacations, I used Hotwire.com to book my hotel. Hotwire is really nifty. You never know the exact hotel you'll be staying at until you put in your credit card information & actually book the room. The cool part is, you choose the approximate location you'd like to stay & Hotwire will give you a list of 4-5 hotels you will potentially get. It might sound scary at first, like who wants to play a guessing game when it comes to traveling, but I assure you, I have never had a bad hotel, a bad experience, or a lousey vacation. Get this, my last hotel stay with Hotwire.com, in Chicago for four nights came to $418. Total. Landed. $100 a night in the city?? Unheard of. With all the money I save on hotel stays, I always have extra cash to spend during my trip! The little things really do add up.
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For now, I've got to go get some R e s t & R i e s l i n g.