Chicago Vacations

travel ideas for chicago - the chicago skyline and waterfront
Chicago is a great destination: a vibrant city full of iconic sights, world-class cuisine, local tastes, annual festivals, and a creative culture all situated waterfront on beautiful Lake Michigan. No matter what you plan your tip for - a romantic getaway, group trip, family vacation or one of Chicago's great events - you will fall in love (again) with the Windy City.

Chicago is a destination in itself, but it can also be your gateway to lake vacations just outside the city and in nearby Indiana and Michigan.

Sightseeing in Chicago

Chicago preserves a rich part of America's industrial and cultural history. Immerse yourself in the architecture, museums and cultural venues; stroll the vast public parks and enjoy the iconic sights that make Chicago a favorite place to stay, see and play. Some of America's favorite sports teams call Chicago home, and even if you don't see one of them in action, you can tour the venues. Don't miss seeing Wrigley Field, home of the Chicago Cubs for almost 100 years. (Read more on things to do in Chicago.)

In the Heart of the Midwest

The official starting point to the Historic Route 66 is Grant Park, and Chicago is still a great hub for road trips of all kinds. After spending a few days taking in the sights, sounds and tastes of the city, hit the road for a week at a lake house or a fall leaf peeping tour of the Midwest. Whatever brings you to Chicago, you'll find tons to do and see here.


Downtown Chicago Vacation Rentals

Best Choice in Chicago: Guest Favorite with Raving Reviews! Email Now for Info!

You just found the perfect escape...Chicago's newest and most exclusive, luxurious residence will make your business or vacation travel the memory of a lifetime. City of Chicago license #2233207. Free garage parking! Offering an oasis of tran...

Chicago Luxurious Vintage Vacation Condo

Residnence on the Avenue. A Spacious Vintage condo in a stunning 1928 Art Deco building on a tree lined avenue. We are a fully licensed vacation rental #2087704 and 1 of only 73 licensed vacation condos in Chicago! A very quiet and secure 4 unit b...

Magnificent Mile, Gold Coast Luxury Brownstone Downtown Chicago Vacation Rental

Another First Class Chicago property! City of Chicago Vacation Rental License #2125365. Rent Legally! You've found it! Location, Location, Location! An historic 1890's brownstone in the heart of the exclusive Gold Coast where Chicago's elite resid...

Amenities Galore, Amazing Views, 1350 Sq Ft of Luxury! Email Now for Info!

You just found the perfect escape...Chicago's newest and most exclusive, luxurious residence will make your accommodations the memory of a lifetime. Offering an oasis of tranquility within Chicago's pulsating River North district, The Parc Huron ...

Luxurious Condo in Perfect Location ..Sleeps 8..Winter Savings

Enjoy your Chicago visit from one of the best locations in the city. Nearby are great restaurants and bars, shopping, a fabulous park, and a famous award winning bakery. Get out and enjoy the city or relax in our luxurious accommodations. Spaci...

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