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Top Tips for a Weekend Getaway to Chicago

Chicago, Illinois also known as “The Windy City” is the third largest metropolis in the United States. Of course this means that there are a lot of attractions, landmarks and options available to visitors wanting to explore this city. Check out our review on the ultimate top tips for a weekend getaway to Chicago including featured attractions, restaurants and places to stay.

Chicago page


Downtown Chicago

The Cloud Gate

One of the great attractions when visiting any major city is the ability to take either a guided or preferably a self-guided walking tour around the downtown area. Downtown Chicago certainly has plenty to offer including the Navy Pier, Millennium Park, Riverfront District among other landmarks. READ MORE…

Willis Tower

Willis Tower

Located in the heart of downtown Chicago, the Willis Tower, formerly known as the Sears Tower, is one of the tallest skyscrapers in the western hemisphere. If you dare to stand on the glass Skydeck near the summit of this high-rise building, this is certainly worth experiencing. READ MORE…

Medinah Country Club

Including Medinah Country Club as an attraction in the Chicago area is for an avid golfers out there as we experienced the ‘Miracle at Medinah’ in the 2012 Ryder Cup. READ MORE…


Lou Malnati’s Pizza

Lou Malnatis Chicago

One of the most famous pizza chains in Chicago is Lou Malnati’s. Unfortunately our experience there wasn’t the best as our food was not particularly good, but it is worth visiting if you want an authentic Chicago Deep-Dish pizza experience.

Krispy Kreme Doughnuts

Krispy Kreme

I know this is a chain and probably not really a ‘restaurant’ but a great spot for breakfast is Krispy Kreme Doughnuts, especially if you can time your visit there whilst the ‘Hot’ sign is displayed outside because you will be given a tasty, free doughnut before ordering. It’s also a cool experience to watch how the doughnuts are made as they pass along the conveyor belt.

Carnelli’s Deli

Carnellis Deli Menu

Located in the food court at the Navy Pier in Downtown Chicago, Carnelli’s Deli is a great lunch option with great subs. Choose from a variety of breads and fillings and you will be left delighted choosing this spot!


Double Tree Chicago Wood Dale – Elk Grove

Double Tree Chicago

The Double Tree Chicago Wood Dale – Elk Grove is located in a northern suburb of Chicago (Elk Grove) and is about 20 miles from downtown. It is a perfect location to just get away from the hustle and bustle of the major metroplitan lifestyle but still provides easy connections to the city.


If you are interested in seeing more of our pictures from our trips to Chicago, please click on the Photo Gallery link below:

Chicago Photo Gallery

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Alexis @FITnancials

Wednesday 3rd of May 2017

I love Chicago! I used to live there and miss it so much. I dream about moving back one day!


Friday 11th of July 2014

Ooooo! Love Chicago! I actually also went to Lou Malnati's for our deep dish pizza and it was actually delicious!!!! That's too bad you didn't have that great of a meal :(

antonette - we12travel

Friday 11th of July 2014

I just read another blogpost about Chicago a few hours ago and I never considered this place for a visit. Dutch people will usually just go to NYC or SFO but this sounds like a great place to hang out for a few days, or as weekend trip. Shame it's such a long flight away for us...

Ashley @ A Southern Gypsy

Friday 11th of July 2014

Great overview and tips for Chicago! I've only spent a tiny amount of time there but I loved it. Will be there again in Chicago when we leave from there to drive to LA! :)


Friday 11th of July 2014

I am sure you will have a great time there Ashley just as you will on your road trip to LA (very envious of that trip by the way!). We always love returning to Chicago despite the fact the majority of the time we are just passing through either Midway Airport or O'Hare.

Kathryn Burrington

Friday 11th of July 2014

I love doughnuts but the thought of having them for breakfast seems so very wrong. Reminds me of when I saw my French lodger tucking into a chocolate sponge pudding for breakfast - I was shocked! ;-) This does bring back memories though of my first job while I was a student which included making doughnuts. They taste so very good freshly made.


Friday 11th of July 2014

I thought the exact same thing Kathryn before I came to USA! But over here they have doughnuts for breakfast all the time so I figured it was worth a shot! Certainly gives you a sugar rush for the rest of the day.