If you crave a night of activity, fine dining and beautiful skylines, then Chicago is for you! This Chicago, Illinois travel guide suggests that you book your vacation rental in advance, especially if you want a Chicago luxury vacation, because this booming city is booked early! Find yourself in downtown Chicago vacation rentals, this year and next, and you will luxuriate in the fine architecture and class of a city that rivals New York City in nightlife opportunities and dining attractions.

What to Do

Chicago Travel The Chicago Children’s Museum is a lot of fun for educational excursions and for any precocious kid who likes to explore new things! There’s a dinosaur expedition, Water Ways, and a tree house that young kids will adore! For a second educational day on the town, try the Artifact Center at Spertus Museum! This hands-on experience will teach you about archeology as well as the ancient Middle East. There are 12 dig sites that you and your kids can enjoy all day long!

Navy Pier is a popular destination, with its tribute to the world’s first Ferris Wheel, a carousel, and other fun carnival-like attractions, this is somewhere you will love to go when you are wrapping-up your day. With 50-acres of parks and an IMAX theater, you will have no trouble convincing any member of your group to go to Navy Pier.

See Chicago from the tallest building in the world! The Sear’s Tower waves in the wind at 1,700 feet high! Look down at the Downtown Loop, or find your vacation rental from this stunning sky deck.

For daytime fun, go to the Deep River Waterpark on East Lincoln Highway in Crown Point, Indiana. It’s the favorite water park of all of the contiguous states, and it offers discount group rates and family packages. Later that night go to the Hancock Observatory on North Michigan Avenue. From 1,000 feet above the city you can enjoy the open-air experience and a wall of Chicago’s history. There are 3-D talking telescopes that create real sound effects, and Sky Tours audio tours that will guide you through the exhibit.

Catch game of baseball at the famous Wrigley Field, or just catch a frisbee in Millennium Park.

Visit 6,000 aquatic animals in their “natural” habitat at the Shedd Aquarium, which has been open since 1929! There are more than 700 different species for you to goggle at and make faces at through the glass.

Back to top

Where to Shop and Eat

Chicago RestaurantsPenang Malaysian Cuisine is a restaurant named after a tiny island in the Malay Peninsula. This is a place to stop-in if you want southeastern Asian delicacies and dishes you only think you’ve previously tried, like shrimp tempura (done right!) Red Light, a similar but more beautifully décored dining establishment, offers Chinese, Vietnamese, Malaysian and Thai, and everything they offer is scrumptious!

Featured in Rachel Ray Magazine for its wonderful, acidic but mayonnaise-free coleslaw, Smoque BBQ has also been featured in Gourmet, and in a Food Network program, too! A restaurant this famous has to be good, and it is! The ribs, pulled pork, brisket, and sauces are tantalizing and perfect, and the Texas sausage is one of a kind.

For French food, try Bistrot Margo, with its lovely, subtle décor and snooty servers who make you feel like you’re really in France! From the crème brulée to the profiteroles and extensive listings of boutique wines and gourmet sauces, this restaurant is a crowd-pleaser. Well, except for the snooty service! If you want the gorgeous French food and décor without the pompous waiters, then Café Bernard is almost as good, but more diverse in the dishes it offers. And, the service is always great.

For a fun night out on the town, before you hit the serious clubs and start getting jiggy, try the Old Oak Tap on West Chicago Avenue! It’s a great place for private parties and fresh, local brews in taps that are flushed so often that you taste nothing but the brew.

Ladies will love Agent Provocateur’s famous style and imaginative cuts. If you need lingerie to continue the trend of luxury and class during your Chicago retreat, then this boutique-style shop will provide you with just enough frill and sass!

For something you can wear outside, Krista K Boutique offers lovely, upscale women’s clothing that you will adore. From denim to maternity, jewelry to shoes, this boutique has it all! Or, if you want something a little more cozy, Berry Natural Clothing sells organic cotton tee shirts that you will want to have made into sheets! Everything is so touchable and luxuriously soft that you will want a shirt for each day of your vacation in Chicago.

Something else in Chicago that’s unique are the fur shops. If you want a head-to-toe minx, or a muff, or earmuffs, or even a fur purse, Chicago will provide you with as many fur shops as you can bear to shop in. The prices are fair, but the styles are amazing.

Back to top

When to Visit

When to VisitOf course snow is beautiful, but if you don’t want to be wading in it on your Chicago luxury vacation, then you should plan to visit during one of the other three seasons. Winter in Chicago is, alas, very harsh and cold. Expect biting, painful winds and knee-deep snow during the height of winter in Chicago.

If you choose to visit this fascinating city during the spring, you will be pleasantly surprised by the light flowery scented air and blooming trees and flowers everywhere. Chicago is a city of concrete, like most large cities, but it’s also gorgeous and blooming in the spring, because the city planners generously set aside lands for parks and extra greenery.

In the summer Chicago is hot, like everywhere else, but it’s not too hot to enjoy a stroll through a garden, or to dine al fresco at night. The best season, however, is autumn in Chicago. If you like to see the leaves changing, and avoid the tourist crush of summer, then fall is the time for your vacation in Chicago! The weather is ideal, the subtle canvas of colors in the trees is appealing, and Chicago vacation rentals are often being rented at lower, or bargain rates in the fall.

Back to top

What to Bring

When you go to a city as chic and lovely as Chicago, you should bring your finest clothes for the fine dining you would like to experience. Between the opera and symphony, the ballet and theatre, you will find ample opportunity to show off your new jewels, Jimmy Choo’s, and anything else you’re proud as a peacock to wear! People in Chicago tend to dress up for nights on the town.

If you want a more laid-back, or family style vacation, that’s possible to in the Windy City! Chicago does require a wind beaker, though, if you plan to visit in early spring!

Back to top

Local Services in

Cruise Chicago! Really, with Cruise Chicago, you can do just that! Private chartered cruises of all kinds launch every day, accommodating groups from 50-150 people. This is not the cruise you saw on "The Office," this is a luxury cruise that will make you giddy with gaudy fixtures and pleasing service.

Chicago Neighborhood Tours can probably explain to you why so many tourists are standing still and staring straight up into the sky. It’s not raining meatballs, it’s the beauty of the architecture! Uptown, Greek Town, Chinatown, Beverly Hills, Pullman neighborhood, and Devon Avenue will all be explored on this great, affordable outing.

If you aren’t traveling in a group of 50 or more, but you would still like to experience a luxury cruise, Odyssey will take care of you for an elegant lunch, brunch, or dinner. There are also moonlight cruises! All of these cruises have great food and live music.

Why not climb onto a bike and follow the footsteps of Barack Obama, and learn about the presidential path from here, to the White House! Presidential Bike Tour is an easy 2.5 hour ride that’s both educational and inspiring for people of all ages. Tours leave twice daily.

Other services, including overnight dry-cleaning, food delivery, private tours, either walking or in chartered yachts, and masseurs who will gladly come to your Chicago vacation rentals to pamper you with the latest fad in massage therapy are all available services in Chicago. This is the city that will give you anything you will ask for!

Back to top

What to Know

The 1983 World’s Fair took place in Chicago in The White City, which was a mini city structure built specifically for the fair. Most of the buildings have been removed, but there spirit of worldliness and the mystery of a fair that fascinated the entire world still hangs in the air in Chicago, and you can feel the palpable excitement in the night’s air. The world’s very first Ferris Wheel was designed specifically to be the crown jewel at the fair, to compete with the Parisian world fair’s Eiffel Tower.

This city that used to be the capital of industry has become a modern gem that seems like the epicenter of the world. From the elegant streets designed by Frank Lloyd Wright to the tall skyscrapers and parks that rival Olmstead’s Central Park in New York City, this is a city that makes everyone feel a little higher-brow and special, just for being able to vacation in Chicago. Chicago luxury vacations are available on Vacation Rentals, at VacationRentals.com, where you save by booking a rental property that's a bargain next to comparable hotel’s rates, and without the hotel hassle of crowded lobbies!

Back to top

Getting to

Chicago O’Hare International Airport is unavoidable if you have ever had a layover in mid-America, so you are already familiar with it, most likely. If not, then know that Chicago O’Hare is an airport that is well designed and efficient, even though it is huge. You could get lost and spend a day wandering all of the corridors like Tom Hanks in Terminal, but if you follow the signs it shouldn’t be a problem! Chicago Midway Airport is also available for your Chicago vacation rentals, but it may be more expensive compared to the O’Hare hub!

Once you have landed in the city, you may want to rent a car, because Chicago is such a large, dynamic city that you will want to zoom to and from your destinations without the hassle of waiting for public transportation. But if you like public transit, then there are an abundance of bus routes, and other means of public transportation. You could take taxis all day and night without a problem, but they are quite expensive in Chicago (hence their over-availability!)

If you are feeling fancy, you could arrange for a limo driver to pick you and your partner up from the airport, and begin a Chicago luxury vacation before you luggage has even hit the conveyor belt!

Back to top

Why Vacation Rentals?

For a Chicago luxury vacation, there really is no better option than vacation rentals! Save cash while enjoying the exquisite privacy of a property that is owned by one person, rather than a corporation. Any amenity you can imagine, you can have. Whether you would like to have a private balcony view of downtown Chicago, a private luxury sauna or hot tub, a heated pool on your penthouse rooftop, or a fully stocked kitchen that a steward has prepared with the foods you like before your arrival, you can have it! The nightly rates for the most affordable Chicago vacation rentals are so low that they could suit any budget.

If you want to look out of picture windows and see the expansive horizon of Chicago, then book your vacation in Chicago today! Stay in a lovely Frank Lloyd Wright designed suburb in a gated community, or in an elegant loft that screams chic, and know that you are saving money hand over fist compared to your compadres who are staying in local hotels. Enjoy having a full kitchen at your disposal, and save even more money by cooking for yourself. Whatever you would like to experience during your trip to Chicago, you can book it, and this Chicago travel guide wants you to have it!

Back to top

You might also like...