Chicago, Illinois: A Destination Guide To The Windy City!

Cloud Gate - Chicago bean

Planning a trip to Chicago??

Chicago is a very underrated city. Minus the winter, Chicago is pretty perfect, especially for visitors from other countries. Most foreign travellers visit Los Angeles, San Francisco, and New York City and leave out Chicago which is a shame. In fact, it’s my favourite American city. 

Why I love Chicago!

  • It’s easy to get around via public transport
  • The food scene is incredible (warning: you may gain 10 pounds on a week visit)
  • If you’re a guy and you’re into sports, it’s a mecca with the Bears, the Bulls, the Cubbies, and the Sox.
  • The architecture is amazing!
  • There are great museums along with great cultural events like festivals, musicals, dance, and theatre.
  • And last but not least, Chicagoans are so nice.

Air Bnb

Where To Stay

The last few visits to Chicago I have stayed with friends. In the past, I would always stay in hotels. One hotel I can recommend is the W Lakeshore. The W Lakeshore is right by Lake Michigan making it an ideal location in the warmer months but a bit of a trek when it’s cold. Taxis or Uber are definitely needed in the winter. If you stay at the W Lakeshore, book a spa treatment at their Bliss Spa. It’s amazing.

Other hotels I’m keen to try are the James, the Langham, Public, and the Virgin Hotel. Hopefully next time!

Use this portal to look up Chicago hotel rate with cancellation

What To Do

A great thing about Chicago is it’s easy to use its public transportation system. You can take the bus or ride their version of the subway called the EL (elevated line) seen below.

El Train In Chicago

Taking the El

Millennium Park

Here are some photos from an afternoon at Millennium Park. It’s a public park space along the Lake Michigan shoreline in the Loop area of downtown Chicago. It is a tourist attraction but it’s awesome and a can’t miss part of the city.

Millennium Park Crown Fountain Chicago

Crown Fountain, an interactive public art and video sculpture in Millennium Park

Millennium Park Crown Fountain

Crown Fountain’s video changes and features local residents’ images and is also a water park.

Jay Pritzker Pavilion - Gehry

For all you architecture fans!! The Jay Pritzker Pavilion by Frank Gehry

Cloud Gate - Chicago bean

Cloud Gate aka the Bean!

Cloud Gate Bean Chicago

Underneath Cloud Gate aka the Bean

Cloud Gate Reflections Chicago

Reflections of the city onto Cloudgate

The Bean - Chicago

My friend Danny and I taking our selfies against Cloud Gate!

Cloudgate - Bean Selfie Chicago

Up close and personal with Cloud Gate

Must do 

One thing I recommend is the architectural boat tour. I’ve taken it but alas don’t have my old photos. I would totally do it again!

Chicago Architectural Boat Tour

Boat touring!

If you don’t take the boat tour, just walk around downtown. It’s very manageable and safe. You’ll see some fantastic architecture like the famous Marina City Towers. People think that they are parking garages because you can see cars parked but it’s a mixed-use building. There are offices, businesses down below, and apartments.

Marina City Towers Chicago

Marina City By Bertrand Goldberg. Probably one of my favourite buildings in the world.

Wrigley Building

The Wrigley Building

Chitown View - Aon Building

There’s a load of great views like this one from the Aon Building. (Excuse the old, low res photo)

I’ve yet to take a picture at the Willis Tower aka the Sears Tower (black building seen above). I’ve had lunch there and even gone as a child but I haven’t gone on their Skydeck. Something to do for next time! There’s a lot of art in public spaces in Chicago. One example is this piece by Alexander Calder in front of the Federal Plaza.

Flamingo by Alex Calder

Flamingo by Alexander Calder


Gorgeous Chicago at dusk

Sports are a huge thing in Chicago. Even if you’re not into sports it’s fun to catch a game. I’ve yet to catch a Bulls game and I love basketball. I have caught a Chicago Cubs baseball game at Wrigley Field. It’s so fun to eat peanuts, drink beer, and cheer on the team with locals.

Wrigley Field Cubs

Go Cubbies!!!

If you’re a fan of art there are several notable museums and galleries in Chicago like the Art Institute below or the Museum of Contemporary Art.

Art Institute

Can’t-miss the Art Institute which is next to Millennium and Grant Park

Where To Eat

Pot Belly Sandwiches

I’m not all fancy. I love Potbelly’s, which is a Chicago sandwich institution now seen in other cities.

Wow Bao

Mongolian beef bao

Wow Bao dumplings! It’s one of the best budget-friendly snacks around Chicago! I grab a couple of these when I’m shopping at Water Tower Place to tie me over till the next meal.

Wow Bao Dumplings

Coconut creme filling bao

Italian Beef

There are some Chicago-specific foods you need to try! One of them is an Italian Beef. Italian Beefs are another Chicago specific dish. It’s a sandwich with roast beef, meat drippings on an Italian roll and topped with giardiniera (pepper mix). It’s so good! I’ve had them at Portillo’s but try Al’s Beef.

Garret's Popcorn

Have you ever had Chicago-style popcorn? It’s a mix of caramel and cheese popcorn. Try Garret’s if you like popcorn! Several locations around the city but they this their stand at O’Hare airport.

For budget-friendly and quick eats, I hit up Big Star for tacos. My friend Christian and I just ordered from their pick up window and ate on some benches outside rather than waiting for a table. Then we hit up a few bars in Wicker Park.

Big Star Tacos

Pork belly tacos at Big Star in Wicker Park

**Now open in Logan Square, check out Chicago Distilling. Haven’t been there yet as it just opened but my friends opened it up and you’ll definitely find me here when I’m in Chicago!!!

We ordered some pizza from a place called Pete’s while I was there. Doesn’t look so epic but it was delicious. In Chicago, they slice them into squares.

Chicago pizza, to me, is great because it’s not soggy. When I’m in NYC I will often ask pizzerias to keep my slice in the oven for another minute or so (well done which sounds kind of funny). Chicago pizza has a more cooked crust and its sprinkled with cornmeal. It’s awesome.

For deep dish pizza, my go-to place is Lou Malnati’s. There are several locations throughout the city. There are other options like Uno’s, Due, Giordano’s but I love Lou’s! They have thin crust too which is awesome. My favourite deep dish is the spinach pie.

Mid-range to higher budget dining options:

While I was in Chicago, I dined at Chef Stephanie Izard’s (winner of Chicago Top Chef edition and James Beard Best Chef Great Lakes winner) popular restaurants Girl and The Goat and Little Goat Diner. Such great food! Big lines or hard to get reservations so planning ahead is a must!

Dinner at Girl And The Goat with friends:

Girl And The Goat


Girl And The Goat

An old-fashioned is a must :)

Girl And The Goat

We ordered the bread. People complain because it’s not free. It’s worth it!

Girl And The Goat Chicago

I always order the pork belly!

Girl And The Goat

Another pork belly dish but this one was a crudo with kampachi

Girl And The Goat

Diver Scallops

Little Goat is Chef Stephanie Izard’s casual eatery just down the road. We popped in for brunch one day.

Little Goat Diner

Smoked Corned Beef Hash With Poached Eggs

Little Goat Diner

Club sandwich

Little Goat Diner

Goat Chili Cheese Fries

Little Goat Diner

Awesome vintage modern interior

Little Goat Diner

Inside Little Goat

Due to its popularity, there is a wait here so plan accordingly!! Luckily there’s a La Colombe Coffee down the road where you can wait and have a coffee.

La Colombe Coffee

Iced Coffee at La Colombe

A place I try to go for breakfast/brunch if it’s not busy is Lula Cafe. Their standard is still pretty good after all these years. It’s in the Logan Square neighborhood.

Lula Cafe

Lula Cafe breakfast burrito

Lula Cafe

Lula Cafe French Toast

My friend Mike took me to Longman and Eagle one afternoon. It’s a bit hipster but it was fine in the day time. It’s a hotel with a bar/restaurant and we stopped in for lunch.

Longman and Eagle

Cuban sandwich at Longman & Eagle

Longman and Eagle

Hamburger at Longman & Eagle

What are your Chicago favourites?  Leave them in the comments!



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Destination Guide To Chicago

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