Today we're bringing you tips on the best ways to enjoy a vacation to the Windy City. Take a look at our Chicago vacation packages, read our guide to your stay and book a trip today!

1. Day One: You arrive in Chicago, grab your luggage and are off to your home base for the next several days: the Chicago Marriott Downtown Magnificent Mile. It’s a big place, providing easy access to all you’ll see and do on this trip. Once settled in your room, you head right out for a sunset dinner cruise. Onboard, enjoy the top-deck lounge, plated meal (no buffets on this vessel!), and watch the Chicago skyline pass slowly by while gliding along the shores of Lake Michigan.

2. Day Two: After a restful night, you’re up (relatively) early and initially going to 360 Chicago for what will literally be the high point of your visit. Perched 94 stories above the Windy City, 360 Chicago provides commanding views of Lake Michigan and Chicago's skyscrapers, including the famous Willis (aka Sears) Tower. Once back down at sea (er, lake) level, it’s time to explore the Magnificent Mile, a 13-block stretch of Michigan Avenue that’s truly one of the world’s great avenues. Have a nice lunch at one of the more than 250 restaurants, then browse through some of the 400-plus shops. Just don’t shop until you completely drop – you’re less than halfway through the trip.

3. Day Three: The Art Institute of Chicago is the second-largest art museum in America and is not to be missed. Located in Grant Park, the museum features an extraordinary collection of Impressionist, post-Impressionist, modern and contemporary art from such masters as Monet, Renoir, van Gogh, Picasso and Pollock. After making your way through the museum, head over to Buckingham Fountain, take a seat and wait just a few minutes for the water display – they’re scheduled every 20 minutes between April and October. You’re now at the centerpiece of the park Chicagoans refer to as the city’s “front yard.” Enjoy it.

4. Day Four: It’s your final full day and you’re keen to experience a little bit of Chicago as the locals do. Set off on foot to the legendary Palmer House Hotel, then over to the Millennium Park area, a modern town square with a collection of art, architecture, and gardens. Next, take a leisurely stroll along the Chicago River – the key reason that the city became an economic powerhouse. Punctuate the walk with quick stops for samples of some of Chicago's favorite foods, such as pizza, hot dogs, brownies, and of course beer from a local brewery. As Chicago-based film reviewers Siskel and Ebert used to say, two thumbs up!