I lived in Chicago for 26 months and it is easy to fall in love with the city from day 1. While it is not New York or LA in terms of prestige and glamour, it has its own unique style from its people, city architecture and delicious treats that would captivate your senses. If there is one love or hate relationship you will have with the city, it will be the cold weather.

I wrote this post with the intention of collating information for those who are planning to visit the windy city.

Location and People

Chicago is part of Illinois in Central North America. Time is at -6 GMT and adopts DST (daylight saving) during March to November.

Folks waving to people taking the river cruise.

Chicagoans could be the most polite and genuinely friendly Americans I have met. From the folks making small talk on elevators, to people who will smile and greet you randomly. They also take strong pride for all of their sport teams.

The only adverse thing I noticed are the panhandlers and beggars. Some just lay down on their own spot, while there are those that walks around, all dressed up, starts chatting you up — and the next thing you know is they will ask for some change. Don’t worry, they are not aggressive, but they seem to be almost in every corner of the streets along downtown.

Safety and Security

Chicago is one of the places I felt safe. Coming in from a country and a hood where surviving on getting mugged and other crimes are part of daily routine, I know how to be cautious. But I haven’t felt that need turn up my shield that way here in the city.

I lived in the Loop and Lakeview East districts and I can walk on the streets with my SLR camera exposed even at late nights without fear of getting mugged. Still, I would not recommend the same confidence I had to everyone, especially those that are new in town.

Police during the Lights Festival Parade

Note that there are still certain places where I would not recommend travelling solo especially on late nights. The South and West districts of Chicago are places you should be extra careful with. These places has some bad police reputation.

Here’s an overview of its current safety index.

Voltage and Outlet Type

United States has a standard of 120v with frequency of 60hz. Power Sockets available are types A and B. Although the most common in every household is type A.

Currency and Payment

The US Dollar ($), abbreviated as USD, is perhaps the common baseline currency globally. It needs no further introduction.

Within Chicago, modes of payment are mostly thru credit / debit cards although cash is still accepted. NFCs including Apple and Google payments are also available at some establishments. Money exchanges are available within airport and banks within the city. ATMs are almost in every 3 blocks and is dominated by Chase and Bank of America.

Best Period To Visit

This will be subjective, but I highly recommend going there in summer. Preferably within July all the way thru August. This is when a lot of events happen that would certainly spice up your itineraries.

The months of September to December is when the events subside as students end their break and the cold starts to rush in. The months of December to March (sometimes until May) is when the snow happens. Temperature could go to as low as 0 °F as the ice melts. March to June can have a bit of a pesky weather as it is still cold and it rains often.

Getting There

Chicago can be commercially accessed in several ways depending on your place of origin. For an immediate reference to different routing and booking options based on where you are coming from, do visit our Chicago travel tips page.

By Plane By Plane By Train By Train By Bus By Bus By Plane Domestic and international flights usually lands you at O’Hare International Airport (ORD). The airport is directly tied next to the city train (CTA) called as the blue line. The cost, as of writing, is $5 with 45 minutes of travel time to the city center. The other option is Cab or Uber/Lyft. From experience, this costs $55-$70 with 20-60 minutes of travel time depending on the traffic. The deciding factor here is the number of luggage you have and how comfortable are boarding it on the train. Don’t fret, this is what I call as the airport line. You will see folks have at least backpack or a luggage and would be happy to share the space with you. But maybe if you have like 3+ bags or the big ones, better get a cab. Another lesser known airport in Chicago is the Midway International Airport (MDW). It is much closer to the city center and accessible thru CTA orange line. That said, the commute time is cheaper and faster than from O’Hare. However, per experience, there are only limited number of airlines operating here and flight is more expensive. By Train If you are coming from a different state, you would arrive at Union station. It is the central hub for regional Illinois transits (Metra) and interstate transits (Amtrak). Union station is on the west side of the loop. By Bus Similarly, for cross state or domestic Illinois travels, you would most likely use the Greyhound bus lines. They have one bus stop at O’Hare and two stations within the loop -- that are approximately 5 blocks apart. From experience, I usually arrive at the station in Harrison Street and depart at the one on Union Station. I won’t recommend a drop off near O’hare unless it is near to your place of stay.

Moving Around

Chicago is a walking city. Ranked 6th in the United States. But compared to Manhattan or SanFo, it is an easier terrain with no boring views. There would always be something to take a snap or stop by on. The only catch is during winter if you can sustain walking on the cold.

Of course, there would be places where you would rather take the public transportation.

Incoming CTA train – Red line.

Bus and Train Bus and Train Ride Sharing Ride Sharing Taxi Taxi Bike Bike Bus and Train This is where CTA (Chicago Transit Authority) comes in. They operate both the train and bus lines in Chicago. They offer unlimited ride passes per day/week or the typical credit-based method thru their Ventra system. You should be able to find Ventra booths to purchase cards in the airport and train stations along the city. Recently, they also opened it up to Apple and Google pay or any bankcard with the “wave” symbol.



To give a quick glimpse of the transport fares as of writing: ** Loop Train – $2.50 ** Bus – $2.25 ** Transfer - $0.25 (up to 2 additional rides within 2 hrs) ** 1-Day CTA Pass - $10 ** 3-Day CTA Pass – $20 ** 7-Day CTA Pass - $33

For more (and updated) information visit the CTA site here Ride Sharing Uber / Lyft are the two available ride sharing service in the city and I have hailed it frequently than a regular cab. I used Lyft often as I found their rates cheaper and some of their drivers are even offering complementary like bottled water and candies. =D Taxi Cabs are available too but I used them rarely. They have CC or Debit card options within the cab where you can swipe yours, although I haven't tried it out and preferred to pay in cash. Bike Yes, there are bicycles for rent and bike lanes within the city. However, I would recommend using it on parks instead for safety reasons especially for tourists who are not familiar with the streets. Don’t worry, the bike lanes here, such as on the Lakefront area, stretches to 29KM or 18miles. You will have a lot of dedicated pavement to cover . For the rates, FAQ and passes, do visit the Divvy site. Remember to download the app to plan your ride and ITI and where are the closest booths to check-in / return the bike.

Top Attractions

Millennium Park Navy Pier Skydeck 360Chicago Shedd Aquarium Millennium Park Millennium Park – Free

201 E Randolph St, Chicago, IL 60602, USA



Located within Grant Park, this is the #1 tourist attraction in the entire Midwestern US as of 2017. It houses the Cloud Gate (aka the bean), Jay Pritzker Pavilion, Crown Fountain and Laurie Garden. Millennium Park Cloud Gate Millennium Park Millennium Park Jay Pritzker Pavilion Millennium Park Crown Fountain Millennium Park Ice Skates Millennium Park Millennium Park Jay Pritzker Pavilion Millennium Park Winter Navy Pier Navy Pier – Free

600 E Grand Ave, Chicago, IL 60611, USA



Pier within Chicago’s lake Michigan shoreline that was formerly the number 1 tourist attraction in Chicago. There is a lot of activities within the complex ranging from a Children’s museum, the Centennial Wheel and lake cruising for a fee. There’s also IMAXX Theater in here with some dining and shopping options. Navy Pier at Night Navy Pier View Navy Pier Tall Ship Windy Docking at Navy Pier for the next tour Navy Pier Navy Pier Fireworks Lake Cruise with Tall Ship Windy Navy Pier from Tall Ship Windy Navy Pier Shop Skydeck Skydeck at Willis Tower (fka Sears Tower) – $24 / adult

233 S Wacker Dr, Chicago, IL 60606, USA



Was once the tallest tower in the world until Petronas tower was built in 1998; and on the western hemisphere for 25 years until the new One World Trade Center was created. The skydeck is on the 103rd floor and has probably the best all-glass see-through boxes I have experienced. Better viewed during dusk. Willis Tower Willis Tower Willis Tower Skydeck View Willis Tower Skydeck View Willis Tower Skydeck View Skydeck Willis Tower 103rd Floor Willis Tower Skydeck 360Chicago 360Chicago at John Hancock Center – $26 / adult

875 N Michigan Ave, Chicago, IL 60611, USA



Located on the Magnificent Mile district. The Observatory is on the 94th floor of Hancock tower. Often compared to Willis’ Skydeck, the experience and views are different and usually has lesser crowd than Willis. I could not recommend the “Tilt” experience given the price over satisfaction ratio. Better viewed during dusk. Hancock Center Hancock Center View from North Beach Hancock Center Hancock Center 360Chicago view 360 Chicago View Navy Pier 360 Chicago View North Beach 360Chicago View Shedd Aquarium Shedd Aquarium – $40 / non-resident adult

1200 S Lake Shore Dr, Chicago, IL 60605, USA



An indoor public aquarium that was once the largest in the world. It was also one of the first to exhibit permanent seawater fish collection. I highly recommend including this on your itinerary despite the price. The lines can go crazy ranging to an hour of waiting. Shedd Museum Shedd Museum Shedd Museum Shedd Museum Shedd Museum Shedd Museum Shedd Museum Shedd Museum

Other Landmarks

Other Museums

Other Things To Do

Food and Budget

Much like any other major cities, food and accommodation doesn’t come in cheap, especially if it is on US dollars. Here are my basic estimates and recommendations.

A sandwich on Subway is around $4-$7 including a beverage. For a decent meal, the average cost within the city is around $8-$14. Do note that for my end, their one serving is already good as two. Yeah, do serve a lot.

Ramping it up to restaurants, buffet and fine dining means shelling out approximately $25 to $50+ depending on your choice of entree. Steaks and seafooods will be on a higher price range.

Pequod's pizza Brunch at Yolk Ramen at Ajida Grilled Steaks at Tango Sur Turkey Leg Meal Cocktails at Big Star in Wicker Park Epic Burger Entree at Cheesecake Factory Ice Cream Cone at Ghirardelli Popeyes Chicken Burger at Kuma's Too Slayer Burger. I believe they are already closed Lobster Meal at Navy Pier Lobster Festival

Fast food / Budget Meals





Best Known For McDonalds Fastfood Burgers and nuggets Panda Express Asian, Chinese Orange chicken Chipotle Mexican Burritos Subway Sandwich 6-inch Subs Naansense Indian Rice Bowls Chick-fil-a Fastfood The sauces and dips Wendys Fastfood Frosty Wingstop Chicken Wings Garlic Parmesan Poppeyes Chicken Fried Chicken Five Guys Burgers Burgers and free peanuts

Personal Recommendations

While even on a budget you should consider trying Chicago’s signature deepdish pizza. They are also proud of their classic Hotdog and Italian beef.

Here are some of the other diners, eateries and the like that had an impact to me.

Nightlife

City of Chicago is filled with bars, clubs and pubs. It also has lounges such as the famous Signature Room in JHC’s 95th floor for lesser crowded nights.

The caveat is that it doesn’t come in cheap. A single shot can cost you around $4 to $7; beers are roughly $5 to $8; and cocktails can set you back from $10 to $15. And don’t get to comfy while you are still sober reading the menu, it doesn’t include the tax yet.

The brighter side is that as you move farther from the city, the cost lowers and the fun doubles. My observation is that the bars at the suburbs area is more likely to attract the local crowd that knows the worth of their money compared to tourists and foreigners.

I intend not recommend any specific watering hole, but do explore Wicker Park, Logan Square, Lake View, Logan Square and Lincoln Park. They are roughly 15 to 20 minutes from the city center and has good neighborhood – consider yourself commuting back intoxicated. If you don’t want to go that far, the West Loop, River North and Gold Coast areas are for you.

One last piece of advice, if you ever get drunk and puked on the cab, that will be an instant $50 on top of your fare. Control your liquor. 🙂

Places to Stay

Since I lived here on rent basis, I haven’t stayed at any hotels. A quick price search on Booking, Hotels.com, Agoda and Airbnb ranges the downtown area to be at $150+ per private room/night. The outside of the loop can go to around $80. Shared rooms and hostels are cheaper.

What I can recommend instead is to stay at least on the north side near the university area. You could go as high as Uptown, as long as it is near the east side (lake) and there is a walking distance to a CTA red, violet or brown line trains. Lakeview East for example is a very good neighborhood where I lived for 5 months. I easily catch a ride to the loop within 10 to 20 minutes by train or bus respectively.

Travel Tips

I have composed a separate post exclusively for this. Make sure to check it out.

Sample Itinerary / Budget (4 days)

Here is the sample itinerary I prepared. My intention is to close out all the major landmarks that are close to each other. But there you may consider tweaking more if you think that it has too much of something that you may consider foregoing (i.e. museums and parks).

This is assuming it is not winter and doesn’t include any other events. 3 Days should be good to see all the favorable attractions with but an extra day would make your itinerary relaxed and would give the room to explore on your own.