Top Tips for a Weekend Getaway to Chicago

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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.Β 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.Β 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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Chris Boothman
Chris Boothman is the co-founder of A Brit and A Southerner. Born near Manchester, England, Chris moved to USA in 2006 where he soon after met his wife and travel partner in crime, Heather. They have since embarked on an amazing journey of travel as they challenge others to follow in their paths of working full-time but also being able to travel frequently! If you have any questions or comments, please feel free to contact Chris at [email protected]


  1. I haven’t been to Chicago yet, can you believe. If I do, I’ll definitely put these attractions and food places on my list of things to do in the city. Thanks for sharing.

  2. I hadn’t realised the Sears Tower had changed its name! Would be very interested to visit the building and its skydeck some time – I imagine that is quite an experience.

    (On a separate note, I can see you have lots of great photos from your trip – would be good to see a couple more placed within the article, rather than just having to click through for the gallery…)

    • Paul, thanks for sharing your comments and I definitely agree with you! I have taken your suggestions and added a few pictures to the various categories to hopefully make this post look a little more aesthethically appealing rather than just having to click through to the photo gallery.

      The Sears/Willis Tower is an awesome experience but I am very fond of skyscrapers and always love to explore them around the world whenever we visit somewhere that has a leading tower. Did you hear about the Skydeck cracking whilst people were on there? Fortunately they have this setup with multiple layers of glass and actually it is designed for one of the layers to crack whenever there is an issue! Probably was a little scary incident for those folks on there though at the time!

  3. Is Chicago where ER was filmed? I think so – I wanted to visit it way back then and yet I still haven’t. Looks like plenty to do, like a mini big apple almost?

    • Anna, yes I believe that is correct that ER was filmed in Chicago within the ‘City Loop’! Frequently you will see shots of the river and the skyscrapers in the background. That’s a great comparison with NYC because along with San Fran, I would say that Chicago and NYC are probably my favourite US cities! They are all great for walking around and exploring – for me that’s what makes a great city!

  4. I keep looking at Chicago as a weekend getaway when one of the local airlines has a seat sale…it looks beautiful so it’s definitely somewhere I would like to see for myself one day. Love the idea of visiting the Willis Tower and standing on the glass floor- we have something like that in Toronto in the CN tower and I love looking down! Great tips- thanks πŸ™‚

    • We also loved our experience at the CN Tower in Toronto (we check out all the skyscrapers and tall buildings whenever we visit a city with one!). You should definitely pay a visit to Chicago because it really is a beautiful city. I would highly recommend heading there and just spending some town downtown walking around, you never know what hidden gem you may come across that we didn’t even mention!

  5. Chicago sounds amazing. I would love to do that downtown walking tour, and trying deep pan pizza. Being from Italy, I love trying the ‘local’ version of pizza wherever I go. I wonder if Chicago would beat Trieste in terms of being a Windy City!

  6. I’m always amazed by the different sides of Chicago. It has such fantastic urban art, architecture and food (can’t beat fresh donuts and those Polish sausages!). Also, I really like your first photo – a nice mix of light and shadows.

    Shame about the pizza experience. As an East Coaster, I am firmly in the thin-crust camp and have never enjoyed the deep-dish pies they serve in Chicago. However, I know that their dining scene is rated as one of the best in the US. So the options are there if you need to avoid the pizza on taste or, in my case, on principle.

    • Thanks for the support! Chicago is an amazing city!! We love visiting and always seem to notice new things on every visit. The pizza experience was a huge fail we are also thin crust people but wanted to experiment and sometimes you win some and sometimes you lose some.. we lost big time lol but had fun doing it πŸ™‚

  7. I haven’t been to Chicago since I was in the tenth grade on a school band trip! It is about time that I returned as I don’t recall too many things about visiting there and it is a whole different experience visiting a place as an adult than on a school trip (although it was fun too!) πŸ˜‰ Thanks for sharing!

  8. 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! πŸ˜‰
    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.

    • 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.

    • 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.

  9. 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…

  10. 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 πŸ™


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