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Beautiful 3 Day Vacation in Chicago

Beautiful 3 Day Vacation in Chicago

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3 Day Vacation Chicago

We recently celebrated our 8th wedding anniversary with a 3-day vacation in Chicago. We enjoyed every moment of our time in the beautiful windy city. Here are a few highlights of our trip including the great food spots, outings, and relaxation. We wanted to focus our short time in the city on trying some of the best places to eat in Chicago, light touring around downtown, and RELAXATION.


Where to Stay

We stayed downtown at the Four Seasons Hotel. If it’s within your budget, I’d recommend a stay at the Four Seasons. This is a sure way to add relaxation and luxury to your time in the city. We were on the 42nd floor of the hotel and the view of the city from our room was spectacular. The hotel staff was gracious and our overall experience at the Four Seasons was completely pleasant.

Visit Millennium Park and See Cloud Gate

Cloud Gate or “the bean”, is a 110-ton reflective sculpture made of a series of highly polished stainless steel plates. It is one of the top things to see in Chicago. The structure is simply phenomenal and the perfect backdrop for an impressive selfie.

3 Day Vacation Chicago

See Magnificent Mile

Walk Magnificent Mile and take in Chicago’s Architecture. You’ll pass many of the city’s beloved landmarks. The Skyscrapers and picturesque view of The Chicago River do not disappoint. It is no wonder the city is an attraction for international travelers, and considered by many, to be one of America’s most beautiful cities. Depending on the time of year, consider The Chicago Architecture Boat Tour. It is rated as one of the top 10 tours in the United States.

 Spend Time at The Spa

We spent one afternoon at the Spa in the Four Seasons. We thoroughly enjoyed all of the services we received here. Get more information on their hours and services here.


Tour a Museum

Take in history, art, and culture at one of the cities museums. We visited the Museum of Contemporary Art. Go here for information about free museum days in the city.

Enjoyed this post? Check out our time in New York City here!

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  1. […] a kid and today I am sharing my favorite homemade Nutella hot chocolate recipe. About a year ago, we visited Chicago where we had hot chocolate from the world’s first Nutella Cafe. Since then, I’ve […]

  2. Jodie says:

    Looks like you had a wonderful visit! We love Chicago and try to visit at least once a year. We havenโ€™t visited the Museum of Contemporary Art yet, though. We may have to visit that next time. We do, however, generally spend a lot of our time in Chicago eating, lol.

  3. Kirsten says:

    I am originally from Chicago, and your post makes me really want to go back and explore my hometown more! I might skip my parents’ guest bedroom and stay at the Four Seasons, though! It’s a great exercise to be a tourist in one’s own town, although this time of year I think I’d prefer to tour sunny South Florida ๐Ÿ˜‰

  4. DeAnna says:

    We visit Chicago a lot. I vouch for the architectural boat tour, it’s fun! Not stuffy at all. Love your pictures, hope you had a wonderful anniversary trip.

  5. Kristie says:

    This is great! Looks like you had a relaxing, fun time! We had 43 hours in Chicago with our kids last spring, and let me tell you, there was nothing relaxing about it except for the 8 hour Amtrak ride to and from Chicago. ๐Ÿ™‚ But it is such a great city!