Vacation In Chicago Romantic

I absolutely loved my vacation to Chicago. The city has a certain charm I’ve only seen in the Midwest. I’ve traveled a lot, but when it comes to attractions like world class museums and buildings, Chicago is second to none. Whether you take your vacation on a budget or with money no object, Chicago will be worth every penny and it’s not all about the food (though you could spend your whole 3-day weekend eating alone and still be full)!

Have you ever had to plan a vacation for a loved one? I’m talking your significant other, parent, friend, or child. In my opinion, there’s no better place to vacation than the city of Chicago.

Chicago is a city like no other; a vibrant and energetic metropolis fueled by the desire to provide people with great experiences.

Who says you can’t plan a romantic vacation that gets everyone out of the country. With most Americans’ finances being in poor condition, lots of people are planning romantic and affordable vacations right here in the United States.

Chicago isn’t just Frank Sinatra’s kind of town, it’s the kind of town that’s got something for everyone. It’s a big city that’s not quite as crowded and fast-paced as New York but still filled with more things to do than you’ll have time.

Vacation In Chicago Romantic

Chicago is home to more than 2.7 million people, making it the third largest city in the U.S. and the largest city in the midwest. It’s lined with urban beaches located along Lake Michigan and is known as the birthplace of the modern skyscraper. A massive fire in 1871 destroyed much of the city center, leaving behind just a handful of structures and paving the way for Chicago to construct one of America’s tallest and most beautiful skylines.

With professional baseball, basketball, football, hockey, and soccer teams, Chicago is a sports aficianado’s dream come true. Catch a Chicago Bears game at Soldier Field. If football isn’t for you, catch a Cubs or White Sox ball game, a round of soccer with the Chicago Fire, the Bulls for a basketball game, or a Blackhawks game for hockey fans.

Chicago isn’t just about sports, though. It’s also a foodie paradise with world-class museums, architectural gems, luxury shopping, and a long list of live music venues and comedy clubs. It’s a place where you’re sure to find plenty of things to do — and eat. Just make sure you save room for deep dish pizza and a Chicago dog.

Time Zone

Central Standard Time

Best Time to Go

Chicago may have freezing winters, but the Windy City makes up for it with warm, sunny summer days filled with live music, neighborhood festivals, and bright blue skies. The best time to visit Chicago is between June and September when the city’s urban beaches are at their best. Runners may want to wait until October when the city hosts the annual Chicago marathon. June brings the well-known Chicago Blues Festival while July brings the Taste of Chicago, an outdoor food festival that allows for sampling of several local favorites. Each August, Chicago hosts the Lollapalooza music festival, the Chicago Jazz Festival and the Chicago Air and Water Show. For travelers brave enough to face freezing temperatures, December brings the Christkindlmarket, a chance to lace up your skates and glide through iconic Grant Park at the Maggie Daley Ice Skating Ribbon and ample opportunities to view Christmas lights at the Lincoln Park Zoo and Navy Pier.

Things to Know

Chicago is a city of more than 200 neighborhoods, each with its own unique character and charm. Chicago and its surrounding areas are collectively referred to as Chicagoland.

Chicago hot dogs are topped with yellow mustard, chopped white onions, sweet pickle relish, a dill pickle spear, tomato, pickled sport peppers and a touch of celery salt. Whatever you do, do not ask for ketchup.

How to Get Around

Chicago is a highly walkable city with an excellent public transit system that includes both trains and busses. Uber, Lyft and cabs are also plentiful across much of Chicago.

Trains: Chicago’s train system is known as the “El” because it’s elevated and runs above ground across much of the city. It’s easy to get from both Chicago O’Hare and Chicago Midway to downtown Chicago via the El.

Buses: Chicago’s train system is extensive, but learn to use its buses and there will be few places you can’t get to via public transit. Bus information is available via text, follow the instructions posted on bus stop signs.

Taxis: Metered taxis are easy to find throughout downtown and surrounding neighborhoods, though Uber and Lyft are likely to be cheaper.

Rideshare: Uber and Lyft are your main options in Chicago. Uber tends to be a little cheaper than Lyft, though that’s not always the case.

Best Hotels

Waldorf Astoria

Entrance of Waldorf Astoria Chicago
COURTESY OF WALDORF ASTORIA

Address: 11 E Walton Street
Phone: (312) 646-1300
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If you’re looking for luxury, the Waldorf Astoria in Chicago is a great place to find it. This 60-story hotel and condo tower is just 10 years old and located in the heart of Chicago’s Gold Coast. It’s designed as an homage to the grand hotels of 1920s Paris, complete with colonnades, a cobblestone courtyard and impeccable service. Rooms are spacious and bathrooms are perfect for lounging in a bathtub full of bubbles.

The Drake Hotel

Palm Court at The Drake, Chicago
COURTESY OF THE DRAKE, A HILTON HOTEL

Address: 140 E Walton Place
Phone: (312) 787-2200
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The Drake Hotel is a luxurious historic landmark at the top of the Magnificent Mile just a couple of blocks from the 360 Chicago and just one block south of Oak Street Beach. The hotel opened in 1920 and over the years has welcomed guests including Prince Charles and Princess Diana, Elizabeth Taylor, Judy Garland, Winston Churchill, Herbert Hoover, and Walt Diskey. Joe DiMaggio and Marilyn Monroe carved their initials into the wood bar of the hotel’s Cape Cod Room, and those initials are still there today.

The Langham

World's Best Hotels in Chicago
COURTESY OF THE LANGHAM

Address: 330 North Wabash Avenue
Phone: 312-923-9988
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This luxury hotel is housed within architect Mies van der Rohe’s last skyscraper. The hotel occupies the building’s first 13 floors, and offers some of the best bathtub views in Chicago. It is located along the Chicago River just a block from the shops of Michigan Avenue. Its Pavilion Lounge is known for its afternoon tea, and the hotel itself is something of a museum and houses 150 pieces of art.

The Peninsula

The Peninsula Chicago's pool
COURTESY OF THE PENINSULA

Address: 108 E. Superior St.
Phone: (312) 337-2888
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If you’re looking for a larger than average hotel room, The Peninsula is the hotel for you. The decor is inspired by Lake Michigan, and the in-room tech addresses every need you could have. Pets are welcome for a bargain $50 a night, and the hotel lobby is far more than what it might seem. It’s also a Michelin-starred restaurant. The hotel has a rooftop pool for swimming with a view.

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