Baby It’s Cold Outside: A Girlfriend Getaway to the Windy City

November 2013

Chicago  Girlfriend Winter Getaway

You have two choices for the time of year to visit Chicago. Although there are technically four seasons there, as in most of the United States, the most well-known are the icy cold winters and the pleasant mild summers. Guess which one I prefer?

Although I have to say Chicago in the winter has some advantages. As it is bitingly cold, it’s not a prime tourist destination so you can get some great bargains on accommodations and you probably won’t have to wait in quite as many lines for the popular venues.

Winter Fun In Chicago

Winter Girlfriend Getaway to ChicagoBundle up with plenty of layers and enjoy the amazing view of Lake Michigan covered with ice and snow, stretching as far as you can see to the horizon. Once you have sufficiently frozen yourself, head for the Museum Campus which is perched right on the shore of the lake and will keep you delightfully entertained for days at a time. The Shedd Aquarium is one of the best in the world and has plenty of exhibits, shows and even a 4-D movie theatre where puffs of air and shaking seats immerse you completely in the experience. Don’t miss the dolphin show in the large auditorium as it’s pretty incredible.

Field Museum Chicago ILNow that you have seen real, live animals it’s time for the world’s largest T-Rex skeleton at the Field Museum, just a short walk from the aquarium. With hundreds of exhibits and another movie theatre, it’s also an amazing place to visit. The Adler Planetarium rounds out the trio of museums at this location and, with three theaters to view the amazing highlights of the sky, you don’t want to miss this location.

Luxury Accommodations in ChicagoAfter trekking around in those icy winds from Lake Michigan all day, you will want a cozy place to spend the night and the Villa D’Citta, a luxury Bed & Breakfast location in the Lincoln Park neighborhood, is the perfect spot. Situated in a historic Chicago greystone on a lovely tree-lined street, this lovely mansion is absolutely amazing. In back is a garage where you can arrange to park which I’m sure was the original carriage house for this “summer cottage” built by a wealthy family for lake getaways in the humid summers in Illinois. With a nice patio and a hot tub located above the carriage, the back area is almost as nice as the interior.

There are a variety of suites to choose from, each lovelier than the last and each uniquely decorated. With an Italian influence from the Italian owners, the entire house is beautifully furnished and decorated. A fresh, hot breakfast is prepared every morning as is common at most B & B locations but this fabulous place goes one step further and provides the fixings for paninis and pizzas in the large kitchen fridge. Make your own hot lunch or dinner and save some money by not dining out! They also have plenty of fresh fruit, home baked cookies and icy bottles of freshly made lemonade and ice tea in the fridge for anyone to help themselves.

However, you will want to leave occasionally for a meal and I highly recommend a fabulous neighborhood restaurant called The Storefront Company. Tucked away in a neighborhood but not hidden from true gourmets, the food is unique and delicious. Try the lamb meatballs; the incomparable garlic bread which comes hot and fresh, baked in a small container; and the dessert platter with some fabulous macarons.

A Fairer Weather Visit to Chicago

For a pleasant summer visit to the city, stay closer to the lake and check in to the Hyatt Regency McCormick Place, located just a short walk from the lake. If possible, book an Executive Suite on a corner, preferably on a high floor as you will have an incredible view of the city and the lake. You will even be able to see the fireworks which are set off a couple times a week from Navy Pier! Plan lunch or dinner at Shor, the restaurant in the hotel which has delicious steaks, chops and seafood.

But for some really incomparable local Chicago specialties, you should book a pizza tasting tour with Chicago Pizza Tours. Spend an afternoon being bussed around the city sampling an incredible variety of pizzas including Chicago’s own deep dish pizza. From delicious Neapolitan pizza with the freshest ingredients we have ever tasted to pizza with the cheese cooked on the bottom into a caramelized and delicious crust, you will feel like a pizza connoisseur after this tour.

Chicago Boat TourAnother fascinating tour is offered by the Chicago Architecture Foundation. A cruise tour, it travels up the Chicago River in a comfortable river boat and includes the amazing history of the many buildings which line the river. Buy your tickets online or purchase them at the dock but if you are buying tickets there, be sure to arrive early as these cruises are very popular and sell out fast. You will see an incredible variety of buildings and architecture – and you may even spot some urban kayakers on the river.

You can’t leave Chicago without a visit to the famous Willis Tower. Formerly known as the Sears Tower, it’s the iconic tourist destination in Chicago and, with 110 floors, you can get an amazing view of the city. Be bold and step out onto the glass skyboxes which extend out over the city and have your picture taken 1, 353 feet in the air!

The Bean, Chicago ILAnother iconic tourist destination is Millennium Park to which you can easily walk after your architecture tour. This park is where the famous, reflective “Bean” sculpture is located and you must take your picture with the city skyline in the background. There is also an incredible fountain in this park where there will be dozens of children playing on a hot day. The Crown Fountain is a work of art which displays hundreds of faces of local Chicago residents on a screen where water cascades and shoots from the mouths of the video projections. The park is located on Michigan Avenue which is one of the most famous shopping areas in Chicago although most of the shops are pretty expensive, so spend some time strolling and people watching in this area.

Chicago Beach GetawayAmazingly enough in this huge city, there are thirty three beautiful beaches within easy walking, biking or taking public transportation distance. Stretching along the shore of the clear and beautiful waters of Lake Michigan, the beaches are a perfect place to spend an afternoon in the summer. It’s wonderful that Chicago has maintained these wide, sandy beaches and not allowed anyone to build on them. They are a part of the Chicago Park District and are carefully kept clean. Five beaches are very popular and somewhat crowded but keep looking and you will find plenty of hidden, quiet and uncrowded beaches to enjoy the sun and water.

Whether you choose to visit the Windy City in the winter or summer – or even in the spring or fall – you will find plenty of fabulous food to eat, and plenty of great places to stay, and plenty of things to do!

Jan Ross is a freelance travel writer who has been traveling the world since way back before she can even remember. Her dad was in the Marine Corps so she is used to packing up at a moment’s notice! She loves writing hotel and restaurant reviews since it means she gets to stay in fabulous places and eat wonderful food. She especially loves writing spa reviews because that means she gets phenomenally pampered and, seriously, who does not like that? She has visited lots of places but still gets a thrill of excitement when she boards a plane, steps into a new hotel room, or sees a new location for the first time. And she hopes that thrill never, ever goes away.

For more information on Jan, visit her website at

3 thoughts on “Baby It’s Cold Outside: A Girlfriend Getaway to the Windy City

  1. Pingback: The Windy City
  2. I’m not brave enough to visit Chicago in the winter (unless I’m being highly compensated) but it’s such a great city! I worked there (although I lived in Boston) for a couple years and always looked forward to going to Chicago. But other than the Shedd Aquarium (which is fabulous) I never had time to sightsee. Your piece made me want to go there as a tourist – I’ll keep an eye on the air fares!

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