About the Social Tourist
This is a blog is written for you – by a longtime resident of Chicago who simply loves this city. My goal is to help you get the best out of your visit to my fine city.
Why you should visit Chicago
This sizeable midwestern city with a population of 2.7 million is an exciting city to hang out. According to the Chicago Tribune, 58 million people visited Chicago in 2018 – a record-breaking number for this city. Conde Nast’s Traveller magazine voted Chicago “the number one big city.”
But why should Chicago be on your travel bucket list?
Here are my reasons:
- The people in Chicago are friendly with good ole Midwestern values – work hard, play hard – always willing to lend a helping hand.
- There is so much to do in Chicago – the possibilities are endless. Culture, architecture, food; you name it. Chicago has it all. You won’t have a chance to be bored.
- Great public transportation. Easy to get around to major (and minor) Chicago attractions.
- Did I mention the food? Chicago is a foodie’s paradise.
It all comes down to this; Chicago is so freakin’ huge. And as a first visitor, I’m sure you have plenty of questions such as:
- where to stay in Chicago
- things to do in Chicago
- safety tips
- transportation options
Are you visiting Chicago this weekend? Read my article, ” Top 5 Things to do this weekend in Chicago”.
Where to stay in Chicago
The city of Chicago has over 77 neighborhoods to choose from for your itinerary’s base of operation. For the first time visitor to Chicago, I recommend staying downtown.
Each neighboorhood has incredible choices when it comes to the best hotels in Chicago downtown. Along with being close to downtown Chicago attractions, staying downtown Chicago makes exploring the neighborhoods outside of downtown more accessible.
Staying in hotels, downtown Chicago, puts you within walking distance of lots of places to visit in the Chicago downtown area such as shopping, tours, attractions, and the lakefront. In the next section, I give you a breakdown of the neighborhoods that make up downtown Chicago.
Warning about booking Chicago downtown lodging
Some hotel chains such as Marriott, Hyatt, and Hilton have more than one hotel located in downtown Chicago. Be sure to check Google Maps for the location to be sure you’re booking the correct Chicago lodging in the area you want to stay. And just because the name of the hotel says “Magnificient Mile or “Downtown” doesn’t mean its actually on or very near that location.
Read my guide to downtown hotels by clicking here.
Not sure which downtown Chicago neighborhood you should stay in? Read up on some of the downtown neighborhoods by clicking on the links below.
Why not stay in the ‘hood?
If this isn’t your first time, I challenge you to get to know some of the neighborhoods outside of the downtown. If you are interested in knowing more about Chicago outside of downtown – start with the following beautiful (and relatively safe) communities.
- Lincoln Park
- Hyde Park/Kenwood
- Near Southside/Bronzeville
- Old Town
- Wicker Park/Bucktown
- Logan Square
What to do in Chicago
There are plenty of things to do in Chicago. You will not get bored. It’s impossible. Most attractions and landmarks are located in the downtown area. However, there are plenty of things going on outside of downtown Chicago as well.
My favorite thing to do is to purchase the Chicago Explorer Pass. It’s a great way to get in a lot of Chicago sightseeing at a nice discount. The Chicago Explorer Pass allows entry into 3, 4, or 5 attractions or activities such as:
- Chicago Field Museum
- Adler Planetarium
- Shedd’s Aquarium
- Willis Tower (Skydeck)
- Art Institute of Chicago
- BigBus Chicago (a must)
- Architecture River Cruise (do not miss this)
- Millineum Park
Where to eat in Chicago
Recommendation: The West Randolph Restuarant District is the perfect area to begin your food journey. Make sure you download the Yelp app to find out where the locals eat.
The downtown area is a foodie paradise! Whatever you have a taste for, you can be sure to find it. To get an overview of the Chicago food scene, I suggest the Chicago Favorite’s Food and Walking Tour offered through Viator (a TripAdvisor Company). Click here to go the Viator.com.
Best time to visit Chicago
Chicago weather is such a significant player that it deserves its heading. It plays a vital role in how Chicagoans and visitors interact with the city.
The best times to visit Chicago and not encounter snow and extreme cold are between late April/May through mid-October. I’ve always said that there’s only two seasons in Chicago; Summer and Winter.
If you’re not intimidated easily by the weather, Chicago during the wintertime can be beautiful as well. Even during the coldest months, there are things to do in Chicago in December.
Are you going to be in Chicago during the wintertime? Read my article, “Things to do in Chicago in Winter.” And don’t forget to bring a heavy coat!
Traveling to Chicago
Two airports service the Chicagoland area; O’hare Airport (ORD) and Midway Airport (MDW). You are going to have plenty of ground transportation options once you land. However, the fastest and cheapest way to get downtown is by public transportation. Both airports are easily accessible by public transit, the Chicago ‘L’ trains.
Traffic from the airports is horrible unless you fly in very early or late (after 7 PM). Unless you love sitting in mind-numbing traffic, I recommend taking the ‘L.’ During rush hour (6 AM- 10 AM and 2 PM – 6:30-7 PM), it can take up to 2 hours to reach downtown from either airport (even though MDW is a lot closer to downtown).
Three expressways run through the Chicagoland area: Interstate 90/94, Interstate 55, Interstate 290.
Chicago has one of the best public transportation in the world. Buses run every 10-15 minutes, depending on the route. Trains run every 7-10 minutes during the day and every 10-15 minute after evening rush hour. For more information, go to www.transitchicago.com.
Recommendation: I’m absolutely in love with the Google Maps app is very useful in navigating Chicago, whether by foot or public transportation.
Other means of getting around Chicago include Uber, Lyft, or Taxi.
Parking downtown Chicago
Parking in downtown Chicago is expensive. Street parking downtown is metered and costs about $6.50 per hour. No need to carry around spare quarters; meters accept credit cards, or you can use a parking app. I recommend reading “Parking in Chicago” by Local Tourist for a great breakdown of parking in the downtown area.
Staying Safe in the Big City
Yes, parts of Chicago can be dangerous. But don’t most cities (both U.S. and abroad) have elements that are considered not safe? With a little street-savvy and awareness of how you’re presenting yourself, you will be fine.
- Just like any city that you visit, always be aware of your environment.
- Try not to appear touristy.
- If you’re like me and love carrying huge-ass purses, make sure the bag has a shoulder strap that you can wear across your body.
- Never leave your purse on the back of your chair. Especially if you are enjoying a meal at one of Chicago’s many sidewalk cafes/restaurants.
- Do not take shortcuts through alleys. No matter how tempting.
- When going out at night, stick to well-lit sidewalks, main streets, and parks. The lakefront is gorgeous at night. Full of good people with neighborly and friendly mid-western values. Join them and enjoy the amazingly beautiful city that is Chicago. I never get tired of the welcoming energy of my city.
- Enjoy yourself.
The City of Chicago Police heavily patrols the downtown area and all neighborhoods. University Police also patrol some neighborhoods such as Hyde Park and parts of Lincoln Park. So like I said…feel free to enjoy yourself but do it safely.
Traveling by yourself to Chicago? 10 Solo Travel Tips!
So I’m not going to lie. Traveling by yourself to an unknown city can feel a little intimidating, a little weird. To make it feel less…umm, scary and weird I recommend the following tips:
- If you’re within driving distance of Chicago…shore up your confidence with a day trip or two or three – to ease into the whole solo travel thing. This is a great way to build up to going on longer trips. It will also allow you to gain confidence in yourself as a solo traveler. Some of my coolest day trips were right in my hometown of Chicago. Every once in a while, I would spring for a room at a nice hotel in the downtown area and do an overnight stay.
- Create an itinerary – that will keep you stimulated visually, creatively, and actively. Create a schedule of your activities to follow but feel free to veer off should you find something along the way you want to explore or try.
- Share your itinerary – with a family member or friend. And it wouldn’t hurt to leave a copy of it in the hotel room or at the hotel’s front desk…just in case. Use technology (your smartphone) to check in with family and friends, periodically while on your journey with a quick text, email, or phone call.
- And speaking of safety – Always, always be present mentally and aware of your surroundings. Go with your gut. If a situation feels unsafe, abort…abort. There’s nothing wrong with being extra cautious when traveling by yourself. As tempting as it might be to wander around a city at midnight (don’t laugh…I’ve done it), it’s probably not a good idea. If you want to go out after dark to take in a concert or the ballet, take Uber or a taxi.
- Travel light – I recommend resisting the urge to overpack and carry a backpack. You will love the freedom of not lugging a suitcase everywhere, and it decreases the chances of lost or stolen luggage. Read my article on the benefits of traveling with a backpack by clicking here.
- Open a checking account dedicated to travel expenses – put away money in an individual checking account for your travels. This will keep you on budget, and you won’t be tempted to gamble away your rent money (done this too in Vegas). Make sure you have plenty of extra cash in this account for emergencies. Having a dedicated travel credit card is excellent also. However, I recommend only utilizing the credit card to hold your hotel room reservation, or for any financial holds, the hotel will likely put on your card. Once a trip is over, you should only have good memories and fantastic travel pictures, not expenses that you now have to pay off.
- Pre-purchase tours and other activities – before leaving for your solo trip. This way, you don’t have to worry about dipping into money earmarked for expenses while on your journey. However, leave room in the budget for those last-minute decisions to do tours or activities that were unplanned. Again, use your smartphone to store digital tickets, i.e., airline tickets, tours, etc. on your device. This will cut down on “oh, shit I forgot my reservation number.”
- I recommend downloading the following apps: Google Maps, Yelp, and Uber.
- Make physical copies of your passport, driver’s license, birth certificate – and any other essential travel documents just in case you lose them on the way, or they get stolen you will have a copy of it.
- Don’t be afraid to ask for help when needed – Chicagoan love to talk about their city, so don’t be scared to ask for directions or suggestions. I’m an introvert, but there have been times during a trip when I’ve struck up a conversation and was rewarded with some fantastic insight into my life or someone else’s.
In short, make Chicago your next travel destination. There are so many great reasons to visit Chicago – fantastic food, culture, famous landmarks, and of course, the people. The possibilities for an attractive, fun-filled good time is endless.
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