Metro Chicago and Southern Wisconsin Vacation Ideas Metro Chicago and Southern Wisconsin - Road Trip Planner
 

Romantic Vacation Getaways in Chicago, Illinois, Milwaukee, Wisconsin Dells, Madison

Things to do / Travel Guide

The Metro Chicago and southern Wisconsin region's cities of Chicago and Madison are both cities in which lovers can feel at home. A Chicago getaway, or a romantic Madison escape, will include some of America's best bed and breakfasts, fantastic food, and a lifetime's worth of attractions. Whether your agenda is a honeymoon, anniversary, or just to get away, the Metro Chicago and southern Wisconsin region is made for lovers.

Romantic Lodgings in Chicago

Chicago is a city of neighborhoods, each with its own character and ethnic history. To get a good dose of Chicago in all its trendiness, the place to be is Lincoln Square.
Thankfully, there are a good number of bed and breakfasts and inns in the neighborhood, and they're all pretty good.

A charming Lincoln Square getaway inn is the China Doll, a place where romance and luxury gracefully intersect. The bedrooms are relaxing and fully furnished, while a steam room and a Jacuzzi with room for two await you in the bathroom. For an especially romantic place to crash, reserve the garden apartment, with its warm brick walls and which opens up to the lovely garden. Breakfast is continental, with plenty of juices and other goodies.

One of the most opulent neighborhoods in Chicago, with scores of stately Victorian homes and mansions, is the Gold Coast. For a stay in a Victorian row house designed in the Flemish Revival style of the late-19th century, reserve a room or studio at the Flemish House. This bed and breakfast is just a few blocks from the Magnificent Mile, so you get the quiet of an upscale residential street and the proximity to where all the excitement lies.

Romantic Activities in Chicago

The Magnificent Mile itself is pretty magnificent. The world's most prominent retailers, clothing, fashion, electronics, and more, are represented here, plus boutiques in abundance. Gucci, Prada, Bloomingdales, Chanel, Barneys, and more – it's all you can do to not get overwhelmed! It's the ultimate place to window shop, the perfect strip to buy a much-appreciated gift for your significant other.

Within the Loop you'll find even more romantic-tinged things to do. Travel to the top of the Sears Tower for dramatic views of all of Chicago, count the scores of bridges over the Chicago River, and admire the bold skyscrapers. The Loop's Grant Park is a fantastic urban park, and Millennium Park is Frank Gehry's ambitious offering to the city. Millennium Park is home to some wild architectural and technological installments, like the Crown Fountain and “the Bean.” Nearby, you can't beat the Navy Pier's Ferris wheel

If the two of you are architecture buffs (but not if just one of you is), tours of Frank Lloyd Wright's homes are a must. Skipping from one of these beautiful and innovative homes to another might be the perfect daytime activity.

Romantic Dining in Chicago

The vast metropolis that is Chicago is home to so many special romantic eateries that eating at only the very most romantic ones might take a month. Nevertheless, for your getaway you probably shouldn't miss a meal at the Capital Grille, as it's one of Chicago's best eateries in any category. The famous items on the menu include the dry-aged in-house steaks and other meats, grilled or otherwise prepared to perfection. It's a busy place, but nonetheless quiet and dignified. The wine list, with over 4,000 bottles, includes selections from all over the world, and there is even a special reserve for the very best wines the world has to offer.

Ready for some excellent Italian food? Italian Village is a Chicago mainstay, more than 75 years old. The house specialty is traditional pasta, like seafood ravioli and fettuccine Alfredo. The ambiance is that of an old Mediterranean haunt, while the service is completely Old World. A big plus is that the restaurant is smack in the middle of the Loop, so all of the Loop entertainment is at your fingertips. Go to a show, maybe at the Auditorium Theatre for ballet or a symphony, where the sound is epic.

One last dining establishment before we send you on your way is Vermilion, preparing a curious concoction of Indian and Latin food. Tasty dishes abound, like Portuguese lobster and vindaloo. There's also a nice tapas selection, and the drinks, with an emphasis on Indian spices, are nothing if not original. They're actually quite good for the experimental crowd. The ambiance is styled but not kitschy, the walls decorated with the faces of Bollywood and Latin stars. The molten chocolate cake for dessert is like the sound at the Auditorium Theatre - epic.

Romantic Excursions in Madison

In a region that includes the great city of Chicago, it's easy to overlook any other gems there might be. But Madison is not one to be overlooked; it's a beautiful city centered around two beautifully-named lakes: Lake Monona and Lake Mendota. These two rounded lakes are separated by just the narrowest stretch of land. That stretch, the isthmus, is the city center, with the State Capitol building, the convention center, and plenty of trendy and artsy neighborhoods. Southwest of the isthmus sit more trendy spots, eateries and so on.

Would you like a room or suite right on the isthmus, just two blocks from the State Capitol and a block from Lake Mendota? Then do your booking at Mansion Hill Inn, an impressive mid-19th century Romanesque mansion bathed in the best Victorian antiques and period furnishings. Floors are all hardwood, and many rooms are centered by a marble fireplace. In the study you find a very curious piece: a canopy bed, whose thick posts support the ceiling like columns. Couldn't get more perfect for a honeymoon.

Another good thing about the Mansion Hill Inn is its proximity to one of the best restaurants around, brought to you by French. The establishment is L'etoile, French nonetheless but so rooted in the fresh Wisconsin produce that the cuisine might almost be called American. Imagine the wild Alaskan halibut with butterball mashed potatoes, sautéed bok choy, and a parsley cream sauce; or the braised beef cheeks with parsnip gnocchi, truffled pea vine, and bone marrow red wine sauce. Yum!

So you've taken a walk to the city center, you've visited the beautiful campus of the University of Madison, and you've strolled the lakefronts, but for some of the most gorgeous views of the city from water, take a pontoon out onto the lakes. Possibly make it coincide with a sunset, but no matter; the gentle bobbing of the water, the seclusion with the one you love, the views - can make such a lake excursion the height of your romantic getaway.

Hot-Air Ballooning in Metro Chicago and Southern Wisconsin

Hot-air ballooning is clearly a romantic way to see the sites, especially when the ride is accompanied by a champagne toast and hors d'ouvres. Hovering over sites like the Sears Tower and Lake Michigan can be an experience perfect to spend with your loved one. The prairies of southern Wisconsin are gorgeous in their naturalness, especially when the view is from 500 feet in the air. Lake Geneva and Sun Prairie, Wisconsin, just outside Madison, also offer great views of southern Wisconsin, including of the State Capitol and the Monona Terrace in Madison.

Metro Chicago and Southern Wisconsin is just a fantastic region, no holds barred. Such cities as Madison and Chicago are excellent places to celebrate a romantic occasion, like a honeymoon or an anniversary. Moreover, if the two of you are looking for a region in which to plan a getaway, you can do no better here. The sights, the smells, the tastes - all make the region a romance haven.

Romantic Vacation Ideas in Chicago, Illinois, Milwaukee, Wisconsin Dells, Madison

Romantic-Vacations-Getaways
Sort By: Rating | Name | Type