The geography and harsh climate of homogenous Middle America limits the availability of diverse, romantic setting escapades around the region. Also, the industrial heartland and its cities have been absolutely decimated by job losses, crime, foreclosure, and the decay of manufacturing. Detroit, Indianapolis, Cleveland, Milwaukee, and St. Louis are not exactly thriving metropolitan areas identified with romance.
Perhaps the misery is what shall make this guide all the more important. Ironically, productive escapism is often critical to preserve one’s sanity and ultimately, his or her relationship.
Certainly, Midwest travel activity centers upon the Great Lakes and the Mississippi River.
Chicagoans are also less inclined to travel throughout the Midwest. Essentially, there is little reason or motivation to exchange the area’s political and social capital for less cosmopolitan environs. Still, we must argue that strong value and a short respite from the Big City hustle and bustle does indeed exist within a two hundred and fifty mile radius of Chicago.
The 250 mile distance mandate is quite appealing in terms of creating the picture perfect getaway fantasy – yet allows for a relatively quick return home if those romantic dreams degenerate towards the ultimate nightmare.
Illinois’ positioning between Lake Michigan and the Mississippi River will prove to be ideal as we present our top-five Romantic Getaways from Chicago:
#5 Romantic Getaway from Chicago: Milwaukee, Wisconsin
Things To Do: Festivals, Art Museum, Lake Michigan, Drink Beer
What Not to Do: Exhibit Chicago Arrogance. Get Fat.
Getting There: I-94 West 90 Miles to Downtown Milwaukee
Milwaukee, Wisconsin is a viable, change-of-pace city directly to the north of Chicago. Mil Town’s 600,000 population is one-fifth the size of the Windy City. Hence, the action will be much more concentrated, with a collegial vibe – the beer and the bar scene parallel Milwaukee’s strong German heritage and influence. Still, pockets of palatable sophistication exist within this southeast corner of Wisconsin.
Milwaukee’s hot spots are downtown and along the city’s North Side along Lake Michigan. Milwaukee Street, Jefferson Street, and the Old World enclave abutting the Bradley Center are electric with restaurants, bars, and clubs teeming with friendly locals.
Milwaukee’s northerly Lake Front is marked with parkland and prominent bluffs that demarcate the shore from the inland city. The Wisconsin Conservatory of Music, McKinley Marina, and Milwaukee’s gleaming Art Museum are all accommodating points of interest.
We must forewarn visitors that the standard fare of beer, brats, and cheese has contributed to the city’s oversized population. In fact, Milwaukee was recently awarded the ignominious Fattest City in the America designation. The scenario is a boon for the self-esteem of curvaceous women struggling with weight issues and the men that Love them. Of course, the line separating shapeliness from unhealthy obesity rests within the eyes of the beholder.
Wisconsin natives do not take too kindly to Chicago arrogance. Interstate 94 through Racine County is a 20-mile speed trap riddled with aggressive troopers hell bent upon ticketing Illinois residents. Land of Lincoln tag holders are more likely to eat the fine than to challenge the ruling in court. Of course, obnoxious North Side Cubs fans that descend upon Miller Park merely to heckle the beloved Brewers are a fashion faux pas.
Lastly, recognize that Green Bay Packer Football is a Religion.
#4 Romantic Getaway From Chicago: Door County, Wisconsin
Things to Do: Bed and Breakfasts, Natural and Peaceful Solitude
Things Not to Do: Argue with Significant Other
Getting There: I-94 90 miles to Milwaukee; continue onto I-43 North 84 miles to Manitowoc; exit at Wisconsin route 42, and proceed 76 miles to Door County. The trip is 250 miles.
Door County is the small Wisconsin peninsula that protrudes into Lake Michigan from Green Bay. The landscape is dotted with lighthouses, beaches, and museums. The area provides excellent, rustic change-of-season fall color, wintertime cross country skiing, and year round outdoorsmanship. This is beautiful country.
Distance is the obvious caveat.
Door County is 250 miles from Chicago and the sparsely populated area spans approximately 50 miles from north-to-south. The uppermost Washington and Rock Islands may only be reached via ferry. The distance, solitude, and lack of action packed, urban environs will challenge the weak relationship. Visitors must ensure that both partners are ready to accept the invitation of natural isolation.
The minor tiff that explodes into a raging tempest would be disastrous in the middle of nowhere – hours away from home.
#3 Romantic Getaway from Chicago: Galena, Illinois
Things to Do: Bed and Breakfasts, Antique Shopping, Quaint Atmosphere, Mississippi River
Getting There: I-90 West 85 Miles to Rockford; Exit at I-39 South and follow to U.S. 20 West at the next junction; Take U.S. 20 – Grant Highway West 80 Miles to Galena. The total trip is 165 miles.
Galena is the only Midwest enclave to consistently appear near the top of every single “beautiful place” list in the United States of America.
Digest the aforementioned piece of information and note the purposeful omission of our “Things NOT to do” header. Visitors that cannot appreciate Galena may not carry the benefits of actually maintaining any semblance of a pulse.
Ice Age glaciers that steamrolled Middle America into flat land prairie bypassed Jo Daviess County and the Upper Mississippi River region – leaving prominent rolling hills, valleys, and bluffs in tact. Galena History has been maintained – in step with the preservation of Northwest Illinois topography.
85% of the buildings are located within a National Register Historic District.
The town that “time has forgotten” served as a prominent hub for all nineteenth-century Illinois political activity. Ulysses S. Grant arrived at Galena as a penniless soldier to work for his father in 1860. The humble gentleman was to leave town and return as the revered Civil War General U.S. Grant. Ulysses S. Grant accepted the 18th Presidency shortly thereafter – without the awkward spectacle of campaigning for the post.
Strikingly, Galena remains unchanged ever since.
#2 Romantic Getaway From Chicago: Lake Geneva, Wisconsin
Things to Do: Skiing, Mansion Tours, Embrace the Chicago Tourist Mindset
Things Not to Do: Saturate Travel Itinerary with Lake Geneva Visits
Getting There: U.S. 12 West; or I-94 West to Wisconsin 50 West at Kenosha. Lake Geneva is 80 miles from Chicago.
Lake Geneva is Chicago’s Playground.
In fact, the earliest recordings of white settlers are synonymous with names that are easily identifiable to the Chicago Native. The area was “discovered” by the Kinzie family traveling between Fort Dearborn and Wisconsin’s Fort Winnebago.
Rugged, Northern Illinois pioneers settled the terrain – before giving way to wealthy Chicago Captains of Industry. The stately, Victorian mansions lording over the picturesque hills and foliage surrounding Geneva Lake serve as the second homes of Chicago’s elite. Indirectly, the city rose to prominence as a consequence of the Great Chicago Fire of 1871. Upper class Chicagoans fled to Lake Geneva in order to bide time amidst the aftermath-rebuild of this disaster.
Lake Geneva is hailed as the “Newport, RI of the ‘West’.”
The enclave is a hotbed for skiing, shopping, and outdoor revelry. Although accommodations range from the intimate bed and breakfast towards the exclusive franchise hotel – lodging is always in short supply throughout the summer months and key winter holidays.
The popularity of the Geneva Lake resort area is its one true downfall.
Couples must tread lightly. Perhaps your beau has already vacationed at Lake Geneva – with somebody else.
#1 Romantic Getaway from Chicago: Southwest Michigan
Things to Do: Sunsets, Lake Michigan Beaches, Wineries, Skiing, Bed and Breakfasts, Antiques; Indiana Dunes State Park and Outlet Mall Shopping are nearby and en route.
Things Not to Do: Let the Secret Out
Getting There: I-90 Chicago Skyway to Indiana Toll Road; Exit I-94 East at Lake Station to Southwest Michigan. Travelers may continue onto I-196, U.S. 31, or the Blue-Star Highway that follows the shores of Lake Michigan. The trip is approximately 100 miles from Chicago.
Interestingly, Southwest Michigan and the Wolverine State publicity do not rival the exquisite merit of these travel locations. The Great Lakes State is largely perceived as a decrepit municipality that has been absolutely devastated by the reeling automobile industry. Certainly, Joe America does not associate Michigan with gorgeous beaches, intimate bed and breakfasts, lush foliage, cherries, romantic villas, and wineries.
Southwest Michigan is arguably the greatest travel secret in America.
The mystery undergirds a quaint atmosphere – where couples may easily relax above the fray of crushing crowds. New Buffalo, St. Joseph, South Haven, and Saugatuck are all perfect getaways lining the opposite shores of Lake Michigan from Chicago.
The area’s climate is moderated by the Great Lake and fertile soils, combined with wintertime snow pack are ideal for growing and preserving grapes. Southwest Michigan is home to a plethora of wineries and trails offering romantic tasting and tour packages.
Adventurous partners may also continue along U.S. Highway 31 to Traverse City – the cherry capitol of the world, and/or Mackinac Island State Park which has been honored by National Geographic as a top-ten location.
Mackinac Island may only be reached by ferry from the I-75 Mackinac Bridge area. Transportation at this locale is limited to bicycling, foot traffic, and horse carriages.