Chicago Travel Blog - Chicago Theater
Chicago Travel Blog - Chicago Theater

Chicago Travel Blog: Table of Contents

Where, How?
Chicago on C&C
Best Time To Visit Chicago
Personal Notes
Where to Stay in Chicago
Let’s Eat!
Let’s Go For a Drink
What to See and Do
Tipping in Chicago
Common Scams & What To Avoid
C&C’s Google Map of the City

Chicago Travel Blog: Where, How?

Chicago, Illinois, United States of America, North America

Population: 2.704 million (2016)

Currency: US Dollar (USD)


O’Hare International Airport (ORD), Midway International Airport (MDW)

Airport Notes: O’Hare International Airport serves several domestic and international carriers. United Airlines is the most common here followed by American Airlines. There are also transatlantic carriers that include British Airways, Lufthansa, Iberia, and KLM. It is one of the largest airports in the world with most connecting flights for smaller cities in the Mid-West running through there. Cancellations and delays are therefore pretty common.

Midway International Airport basically serves low-cost carriers except for a few of Delta’s flights. It is also the largest for Southwest Airlines. It is a better option as it has fewer delays, isn’t as packed and is cheaper. Also, it is a lot closer to downtown. Other airlines that serve it include Frontier, Porter, South Country and Volaris.

Transportation to-and-from the airport: There is an abundance of taxis to and from both airports. They are however quite expensive mostly during rush hours. There are CTA trains that offer direct service to both airports from anywhere in Chicago. They are a better option as they are a lot cheaper and faster during rush hour. You could organize in advance for airport transfers with your hotel. Most of the larger ones have complimentary shuttle vans to either one or both of the airports.

Intra-City Transportation

Downtown Chicago is favorable for walking as it is not congested and streets are wide. In case of extreme weather, the Chicago Pedway System will prove helpful. The best way to see the city though is using public transport. It is cheap and on the most part safe and efficient. You also could choose to drive though avoid doing so in downtown Chicago. Your trip is incomplete without trying the Chicago Transit Authority (CTA) which operates the city’s trains and buses. Chicago’s taxi fares are significantly cheap in comparison to other US major cities. They can be hailed from any street in the city.

A Note on Taxis:

Taxis may not be as easy to find outside Downtown, North Side, Near West, or Near South neighborhoods. You are better off calling one instead.

Just like anywhere, Uber is cheaper and safer. If you don’t already have an account, use this link and get 15 dollars off your first ride!


Downtown is the center for work and play for not only Chicago, but the entire Mid-West. It is also home to Chicago’s most famous sights. The North Side is made up of upscale neighborhoods and has one of the country’s largest LGBT communities. The West Side is fashionably rough and is characterized by its ethnic enclaves, dive bars, and hipsters. The Far North Side is chill and laid-back but hip with its vibrant immigration population. The Far Southeast Side is home to the historic Pullman District.

Navigation tips: Chicago city is easy to navigate with its consistent block numbers all city round. Also, westward is Lake Michigan at all times!

More About Chicago on C&C

Chicago Travel Blog – Best Time To Visit Chicago

Average Monthly Minimum And Maximum Temperatures

Average min and max temperatures in Chicago, United States of America
Average min and max temperatures in Chicago, United States of America

Average Monthly Hours Of Sunshine

Average monthly sunhours in Chicago, United States of America

Average Monthly Rainfall Or Snowfall

Average precipitation (rain/snow) in Chicago, United States of America

Chicago Travel Blog: Personal Notes

What’s This Place About?

Chicago is a very large, unique city that boasts beautiful architecture. Its many neighborhoods and geographical locations are very delimited and it changes rapidly from one area to the next.

The north side boasts several very affluent suburbs, and the town of Evanston is home to Northwestern University, which is a part of the Big Ten NCAA conference.

Between the north side and downtown are a few pockets of very fun, cool, young, mostly white neighborhoods.

Downtown is expensive, glamorous, and where all of the money is. There are huge stores, towering skyscrapers, and the largest companies in the world all have a seat there.

The south side of Chicago is dangerous and is also known as “Chi-Raq” because more people die there from gun violence than in Afghanistan or Iraq.

Chicago Travel Blog – What’s Great and Fun?

Chicago is a sports fan mecca. Baseball enthusiasts have the White Sox on the south side and the Cubs, who play at legendary Wrigley Field, on the north side. Hockey devotees religiously follow the Blackhawks, who share their home with the NBA’s Bulls at the United Center, which is also known as “the house that Jordan built” in homage to basketball great Michael Jordan, who played most of his career in Chicago. Football devotees tailgate and cheer for the Bears at iconic Soldier Field, and MLS soccer supporters can watch the Chicago Fire.

Chicago’s architecture runs the gamut from historical to contemporary. Willis Tower, the landmark Chicago Theatre, the Marina City buildings, the historic Wrigley building, McCormick Place, and the Tribune Tower are all well-known tourist attractions. There is also a group of blues and jazz clubs, famous in the 1950s, that while not really frequented by native Chicagoans anymore, are definitely among the city’s tourist hot spots.

Personal Anecdotes

The place I usually hang out in Chicago lies on North Milwaukee Avenue in the Wicker Park neighborhood. There are wonderful cafes, art galleries, bars, pubs, and some really nice restaurants here.  While a lot of the renaissance food in the United States stems from New York, there are some great spots in Chicago, and many of them can be found in Wicker Park.

Chicago Travel Blog: Where to Stay in Chicago

In the Loop District in downtown is where you will find the best places where to stay in Chicago as well as the majority of the city’s major attractions. The city is large and has more to offer than just the busy downtown district.

For something more tranquil and secluded, the area around O’Hare Airport and its scenery would be a great option where to stay in Chicago, options include: Edward Hotel, Four Points by Sheraton Chicago O’Hare and Holiday Inn Hotel and Suites.

Many of the hotels in the Loop though expensive are worth the price and offer a place where to stay in Chicago and retire away from the buzz of activity in downtown Chicago. Kimpton Hotel Allegro, Hotel Blake an Ascend Hotel Collection, The Palmer House Hilton and LondonHouse Chicago by Hilton, all offer great accommodation and luxury.

The West Side is a cheaper and a more convenient area where to stay in Chicago. It is very colorful and vibrant and Chicago’s most diverse neighborhood. You can book in Ace Hotel Chicago and Royal Living Group.

If you prefer to stay close to the action though, Uptown is ideal place where to stay in Chicago,  littered with jazz clubs that offer live entertainment. Holiday Inn Chicago Mart Plaza, Kinzie Hotel and Dana Hotel and Spa are great options!

Wicker Park area is famous for live music and nightlife, chef-driven restaurants, countless art galleries and amazing hotel where to stay in Chicago: The Robey.

Streeterville offers a lot of entertainment in the form of outdoor recreation at Ohio Street Beach or arts appreciation at the Museum of Contemporary Art. Also, hotels where to stay in Chicago are awesome in this area: Embassy Suites Chicago and Hyatt Centric Chicago Mile.

As for personal recommendations where to stay in Chicago, I can mostly tell you that this hostel is comfortable, hospitable and has a great location: Wrigley Hostel – Chicago. The other hostel I visited during my last time there closed since.

For an affordable stay, Urban Holiday Lofts and FieldHouse Jones are both good quality hostels located relatively near downtown.

Of course, the higher-end hotels where to stay in Chicago are all available, and all of them are in skyscrapers within the Loop. These include Hyatt Regency Chicago and InterContinental Hotel Chicago. They’re all great, but the challenge is to find a very good 3-star place with a reasonable price. I haven’t been able to find such a place, and so when I’m in town, I always browse AirBnb for affordable places where to stay in Chicago. I usually look places in Wicker Park or around Wrigley Field.

Chicago Travel Blog: Let’s Eat!

Famous Foods and Specialties

  • Pizza (in general)…
  • …Deep-dish pizza…
  • …and thin crust, square pizza
  • The Chicago hot-dog (the best in the world)
  • Italian beef

Chicago Travel Blog – Best drunk food

  • Chicago hotdog (Really.)
  • Anything at the Wiener’s Circle

Our Suggestions – Dishes and Restaurants

One of the best restaurants in the world, Alinea, is located in Chicago.

Go to Murphy’s Red Hots for a Chicago dog. Or at the Redhot Ranch!

Note: Murphy’s Red Hots has since closed its doors.

DMK Burgerbar and Fish Bar are good and very popular. Check them out if you’re around Wrigley Field.

Mr. Beef on Orleans is a great spot for Italian Beef. It’s an institution, and there are crazy Chicago characters that roam in and around the place, including the owner!

Bari is another great sandwich maker!

Big Star is a hipster taco joint that has had a lot of influence in North America in the way that taco restaurants are run. It’s quite overpriced, but it’s a cool place!

Check out Longman & Eagle. It’s somewhat affordable and the food is great.

There are superior coffeeshops in Wicker Park. Check out The Wormhole Coffee, Filter Cafe and Caffe Streets.

Note: Caffe Streets has since closed its doors.

I know this isn’t a “normal” restaurant suggestion from me but I really enjoyed my time at Sushi X. It’s a cheapish, BYOB sushi spot with animés projected on the walls and way-too-cool waiters. You have to be in the right frame of mind to go there, but I loved it!

Chicago Travel Blog: Let’s Go For a Drink

What do the locals drink?

Both craft cocktail and craft beer scenes are a bit late on New York and other places but alive and rising!

Chicago Travel Blog – Drinking in public

It’s illegal to have an open container of alcohol anywhere in public in Chicago.

Our Suggestions – Bars and Pubs

Chicago nightlife has a lot to offer from underground bars to rooftop lounges. It also has an infinite amount of blues bars and jazz bars.

But what I personally like the most are dive bars. And Chicago has a lot of them too! Check out both L&L Tavern and Nisei Lounge near Wrigley Field. L&L Tavern is actually quite famous for being the favourite hangout of a couple of serial killers! There are dozens of unique and spectacular dive bars in Chicago. Just Google it!

I’ve enjoyed my time at the Slippery Slope, a nice hipster bar with arcade games that has a dancefloor on the weekends.

Revolution Brewering is a beautiful, large brewpub that offers beers made on premises and generic American food.

In the same frame of mind as the previous suggestion, Half Acre Beer Company offers beer they make themselves and middle-of-the-road food.

Listen to some jazz music at Green Mill cocktail lounge famous for its Sunday night poetry slams. (Not that I’m into that sort of thing, but…)

If you’re looking for something glitz&glam, try The Signature Lounge. It’s a great place to go for a glass of your favorite drink as you watch the city below and sample its gourmet appetizers.

As regular readers of this column know, I don’t know anything about clubs. Sorry!

Chicago Travel Blog: What to See and Do

From the observatory on the 94th floor of the John Hancock Center, get spectacular views of Chicago below.

The Navy Pier, Illinois’ most popular attraction is just the place to visit with family.

Watch the daredevil maneuvers of fighter planes from the North Avenue Beach during the city’s annual Air and Water Show.

The city is known for its live theater and comedy. At improv comedy clubs, tickle your funny bone and laugh your socks off. The Second City has hosted some of the country’s biggest names in comedy including Bill Murray, Stephen Colbert and Tina Fey.

Get a glimpse of Millennium Park and Buckingham Fountain as you walk through Grant Park.

Get atop Skydeck at Willis Tower, which stands at 1,353 feet, and look down at the city

Tipping in Chicago

Just like in most of United States, it is definitely expected to tip because it is how waiters get paid in restaurants. Even if you’ve had bad service, 15% of the total cost of the bill is mandatory. If the service was good, 17-20% tip is normal.

Chicago Travel Blog: Common Scams & What to Avoid

Common Scams

I am not aware of any.


Pickpockets are not a problem, but the regular travel warnings apply.


Great attention should be paid to this section. There is a LOT of crime in Chicago and travelers MUST be aware of the alarming amount of gun violence. Avoid entering the wrong neighborhood at the wrong time. Depending on which area of the city you are in, muggings happen quite often. The city is very segregated and it is said that there are parts of the south side that are rarely frequented by police.

Problematic Neighborhoods

When heading to the south side for a White Sox game or to visit some of the area’s very famous thin crust pizza places, you need to research where you are going and how you will get there very thoroughly. While you don’t need to avoid this area completely, you do need to exercise caution.

How to Stay Safe: Tips and Tricks

Knowing where you are and where you are going is crucial to staying safe in Chicago.

READ MORE: Travel Canada Advisory for the US.

Chicago Travel Blog: C&C’s Map