It started off as a town built out of entirely too much wood. Then fire swept through, causing destruction of epic proportions and the deaths of hundreds. But the result was an immediate rebuilding that transformed the place into one of America’s most important cities.


Chicago Cityscape

Chicago really is a place like no other. Situated on the shore of Lake Michigan, the city provides a surprising contrast to the surrounding vast plains of middle America. Whether it’s the vibrant ethnic neighborhoods, the deep dish pizza and Chicago style hotdogs, or the public art ranging from The Picasso to The Bean, Chicago is a unique city that goes above and beyond its typical association with Al Capone.

There are countless ways to stay busy exploring the city of Chicago, but here’s our list of recommendations.


We almost always choose CouchSurfing over paying for accommodation. Which is what we did for most of our time in Chicago, staying with some great hosts conveniently located adjacent to the University of Illinois at Chicago. But when one of your best friends generously gives you a night at a gorgeous AAA Four Diamond Award hotel, you don’t think twice about packing up and indulging yourself. Our last night in Chicago we stayed at The W, an incredible hotel with phenomenal views of Lake Michigan. Seriously, we could see the lake from our shower. Include that with a feather-bed, down pillows and a five-minute walk to Navy Pier, and you have one happy newlywed couple ☺

A Cruising Couple, W hotel

W, Chicago

Walking Tours

There are numerous ways to walk around exploring Chicago, and you can effortlessly spend a week just getting to know a few of the numerous ethnic neighborhoods. But if you want to stay in the Downtown area known as The Loop, there is a great public art walking tour to take advantage of, compliments of Lonely Planet’s Chicago City Guide. Not only is it free, but the public art really adds to the character of the city itself, and the tour can be done in as quickly as an hour and a half. Along the way, you’ll stop at the following:

1. The Picasso: Noone’s really sure what this piece of artwork represents (after all, Picasso did create it) but come game time it wears a Bear’s hat just like the rest of the Chicagoans.

The Picasso, Chicago

2. The Chicago Theatre: Let’s be honest—how can you visit a city as great as Chicago and not get your picture taken with the famous 1920s marquee?

Chicago Theatre, Chicago

3. The Chicago Cultural Center: Not only does the center have the world’s largest Tiffany’s glass dome on the second floor, there is free wi-fi and a wealth of information about Chicago itself.

Cultural Center, Chicago

4. Cloud Gate: This landmark is more popularly known as ‘The Bean,’ after the shape it resembles, and is a great place to snap photos of the skyline’s reflection. Although most Chicagoans hated it at first, it is now one of the most photographed images in the city. This means be prepared to fight for your image-snapping ground amongst the throngs of fellow tourists!

A Cruising Couple, The Bean

5. Crown Fountain: These fountains provide children with plenty of water splashing pleasure while also displaying larger than life human faces on their 50 ft LED screens.

Crown Fountain, Chicago

A Cruising Couple, Fountain, Chicago

For the complete tour, including directions and descriptions, see the Lonely Planet guide mentioned above. 

Stuffing Your Face

Oh the eating to be done in Chicago! You can easily expand your waistline here if you’re not careful, but every calorie tastes delicious and gives you an excuse to explore the great ethnic neighborhoods we keep mentioning. Some of the most expensive gastronomic adventures can also be found in Chicago, but if you’re on a budget than here are our suggestions:

1. Czerwone Jabluszko (The Red Apple): It’s a polish buffet with every sort of potato dumpling and sausage you could ever ask for. Even if you’re not a Polish food connoisseur, you’re bound to find something you like at The Red Apple.

Polish buffet, Chicago

2. Ann Sather: This Swedish restaurant, located in Andersonville, is known for its Cinnamon Rolls–and for good reason! For $3 you get two massive, warm and decadent rolls covered in all the rich icing goodness you could ever want. After breakfast you can explore the Swedish American Museum next door or head down the street to the landmark Swedish Bakery.

Ann Sather, Chicago

3. Giordano’s: Some say you haven’t lived until you have tried true Chicago deep dish pizza. Well, I guess we can officially call our life complete. Every Chicagoan has their own favorite pizza joint, but we opted for Giordano’s because of its convenient location near our CouchSurfing home. We were more than satisfied with our first  experience, but be prepared that this pizza is seriously two inches thick, and you really only need a slice to fill you up.

Giordano’s deep dish pizza, Chicago

4. A Random Hot Dog Place: We’re not quite sure where we got these hotdogs from, but they were actually much better than we expected. A hotdog ‘Chicago Style’ translates into tomatoes, onions, neon relish, sport peppers, yellow mustard, celery salt and a kosher pickle.

Chicago hot dog

5. Yolk: We love a good breakfast (even if it’s at 1:00 in the afternoon) and that is exactly what Yolk specializes in. We suggest the California Omelette, with avocado, sautéed mushrooms, green onions, tomato and garlic, adorned with a side of two pancakes and fresh fruit. It takes two to finish the generous portion, and at only $9.99 we think that’s a pretty good deal.

Yolk, Chicago


If you need refreshment after all the walking on a hot summer day, head over to Goose Island Beer Company. This Chicago brewery has a constantly evolving beer menu with a fairly wide selection.

Goose Island, Chicago

If you’re out exploring the ritzy Gold Coast, make your way to the John Hancock Center, Chicago’s third largest skyscraper. But don’t pay the $15 to access the 94th floor observation deck; rather, go to the 96th floor lounge for free, where you can use the same money for classy drinks to accompany your top-notch view.

A Cruising Couple, John Hancock Center, Chicago


We love going to see shows, so when we found $18 tickets to see Beauty and the Beast, we jumped on the opportunity. Yes, our seats were a bit in the nose bleed section, but when the show didn’t sell out we were able to scoot down quite a few rows. We thoroughly enjoyed the show in the gorgeous Oriental Theater and really couldn’t have thought of a better excuse to dress up and grab post-theatre drinks.

A Cruising Couple, Beauty and the Beast, Chicago

The Oriental Theatre, Chicago