A Chicago Escape – Things to Know When Planning Your Visit

Chicago – deemed the “Windy City” sits on Lake Michigan is the third largest city in the United States. It is home to the Cubs, a stunning skyline, top notch museums, parks, theater, architecture and if you are a foodie, the city is like a dream come true. It just may be possible to eat at a different restaurant every single day for years and years and something tells me that you will not be disappointed! Ohhh, and the nightlife, where do I start?! It is just something you have to experience for yourself!

I have found myself in this city several times for work and many times for fun, most recently a girls’ weekend! Such a blast and I highly recommend it! Here’s a few tips and things we learned over the years from the locals & just figuring it out…


Planningcan be fun!

  • If you are taking a summer trip, the third weekend in August is always a blast as the Air & Boat Show is happening and it is FREE with plenty of cool spots to view it from, such as the North Shore Beach. (Yes, Chicago does have a “beach” and it is not on an ocean. 😉
  • Every year on St. Patrick’s Day, the river is dyed green. It is stunning to see (have only ever been able to enjoy by pics) and I hear it is a blast celebrating the Irish holiday!
  • The city is just magical in the winter. Lights, snow and good cheer will serve as your backdrop as you explore. Just be sure to bring lots of layers and dress for the weather! The horse drawn carriages are also draped in lights, very “romantical” if that is your kind of thing!
  • Chicago has two airports – Chicago Midway International Airport & O’Hare International Airport. Midway is actually closer to the city and the “L” train has a line directly from the airport into the city. Really easy to navigate. O’Hare is located on the far Northwest side of Chicago and also offers access to the train. FYI – If you are a Southwest flyer, they ONLY fly into Midway.
  • If you choose to drive in and are planning on staying in the city, be prepared to pay for parking at the hotel and everywhere you go. This is something to think about when choosing a place to stay, while you are paying for parking, Chicago is an extremely easy city to navigate on foot, if you are able. There is a pretty big convenience to walking straight out of your hotel to start your day! Staying in the city cuts down on travel time into downtown (especially if you have limited time) and the money you put towards the train, bus, taxi or Uber is used for hotel parking. There will always be traffic in Chicago, it is just a given, so be sure to put some thought into where you want to stay. (FYI – Parking is extremely limited in Chicago)
  • Hotels come at a premium price in the city, but you can find some great deals. Check Kayak Hotel Search for a quick comparison. Don’t forget options such as Airbnb and VRBO (Vacation Rentals by Owner). If you choose to stay a little further out, look for hotels that offer easy access to the “L” train – Chicagos’s rapid transit system. It is color coded by line and truly easy to figure out, plus all of the attendants are super helpful, just ask!
  • Here’s a hotel that we recently stayed at and was literally steps to the train: Renaissance Chicago O’Hare
  • Here’s an option that we stayed at in the city. Perfect location to everything! The Wit – Doubletree

What to see & Do

Chicago truly offers something for everyone and so much more. It just depends on what exactly you are looking for. Here’s a few of my faves:

  • Millenium Park – Gorgeous park to walk through where you can get a glimpse of the iconic “bean” also known as Cloudgate, a public structure by British artist, Annish Kapoor.
  • Super cool photo-op! 081613Chicago w Sissy (16)
  • Before you venture away from Millenium Park, cross the street to the Chicago Athletic Club and take the elevator up to Cindy’s Rooftop Bar.  This open air bar gives you a great place to enjoy a cocktail and the view from above is incredible! No cost to hang out, but please do enjoy a drink! I highly recommend Howl at the Jun — delish! Non-peak hours will give you the least wait and best viewing ability! IMG_20160821_195748205
  • About a half a mile or so further down the road is Buckingham Fountain. For those Married With Children fans, this is the exact fountain in the opening credits. Apparently, there is a light show at night and it does close at 11 p.m. We missed the evening show, but still enjoyed it during the day.  65035
  • Navy Pier – there’s always a ton happening at Navy Pier. While it is definitely touristy, some may really enjoy the Ferris Wheel, shopping, dining and a leisurely stroll along the water.
  • John Hancock Center – another great way to view the city from up above. You can pay for the full experience which includes a “tilt photo” that appears as if you are floating above the city or you can take the other route and go to the 96th floor lounge for a drink & a view. IMG_20160820_173412241_TOP
  • Don’t miss the iconic Chicago Theater Sign – this pic will make for a great souvenir of your trip. Located on North State Street in the Loop area of Chicago. Catch a show while you are there! 081613Chicago w Sissy (27)
  • And, if you would prefer to see Chicago by water, the Wendella Architectural Boat Cruise is an excellent way to see & learn about the city!

And, no trip would be complete without some…

Great Eats!

  • Giordano’s – Original deep dish Chicago style pizza. Head to the Rush street location. Lots of places to grab & drink and digest before you hit up some great spots dance it all off!
  • Portillo’s – home to Chicago style hot dogs, Italian beef, burgers & salads. Oh and don’t miss the chocolate share – they put an entire piece of chocolate cake in it, seriously!
  • Garrett Popcorn – mouthwatering popcorn that hits the spot after every meal. A must try is the mix of cheddar & caramel, my personal fave – almond caramel!
  • Gibsons Bar & Steakhouse – one of the BEST steakhouses in Chicago. Great atmosphere, amazing food with a side of light entertainment & people watching.
  • Billy Goat Tavern – cheezborgers it is! Be sure to ask about “the curse” while you are there. Simple, cheap and satisfying eats at this little dive.
  • Mercadito – great for drinks & fun for dinner
  • Stout – don’t miss this hot spot on Fridays for happy hour!
  • Untitled – speakeasy with live music and a super fun scene. Had a BLAST here! Check it out  after dinner for drinks & entertainment.

As with the “things to do” list I really could go on, but this should give you a nice jump start in planning your getaway to Chicago! Girls trip, Bachelor party or family weekend escape, you will LOVE this city, I promise you that!




XOXO, Renee

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