Chicago is a massive city – covering over 237 square miles. There are roughly 2.7 million permanent residents and more than 48 million visitors to the city each year. There are almost 5,000 restaurants to choose from. You could visit a different museum every weekend and still have leftovers, because we have 60 of them – including the #1 Museum in the World. (spoiler: Art Institute of Chicago). There are over 200 theaters & over 225 music venues in Chicago. Getting around in the city can be a breeze or you could feel like it requires an advanced physics degree. Chicago has 28 bus routes & 8 train routes that connect 146 stations. Over 3,000 bikes spread amongst 300 stations are available to rent by the hour to help you tackle one of the countries most bike-friendly cities. And while Chicago ranks #3 by population in America we’re still home to 8,1000 acres of green space, 580 parks and 26 beaches.

Source: City of Chicago

So how the heck are you supposed to figure all of this out on your short weekend trip or heck, even week-long trip to Chicago? Free Chicago Walking Tours is going to help. We present to you the top 12 resources to “hack” your way to an unforgettable Chicago vacation. These websites are a special selection that will make you you make the most of your Chicago trip by having fun, learning & meeting people.

START HERE WITH THESE GENERAL TRAVEL & CHICAGO SITES

TripAdvisor Chicago – Hear us out first. Free Chicago Walking Tours recommends using TripAdvisor Chicago as a way to start the brainstorming process and see what other visitors did in the city.  There is so much information in one place. From things to do, to restaurants, hotels and short-term rentals. Free Chicago Walking Tours even challenges Chicago-area locals to take a look for themselves and find out what is hot in Chicago.

Wikitravel Chicago – Online since 2003, Wikitravel bills itself as the original crowd-sourced travel guide with over 300,000 destinations, including Chicago. There is so much information here. Free Chicago Walking Tours loves this information because it really doesn’t come with an agenda. It’s simply there – use it as you please. It coves topics you really won’t find on other travel sites. Topics such as staying safe within the city and includes a listing of all of foreign consulates located within the city as well as their address and phone numbers. But there really is so much more than this. if you have an hour or so to spare and have never been to or read about Chicago you must visit this page.

Choose Chicago – Yes, we know. Not really a hidden gem or a secret, but this is a catch-all site that is dedicated to Chicago and it didn’t feel right leaving it off. Choose Chicago has a little (OK, a lot) of just about everything. It can be a bit overwhelming because there is so much information, but used correctly and it can be a real asset. Their Chicago Trip Planner is an excellent place to start for those visiting for the first time or the fifth time.

OVER 30% OF VISITORS TO CHICAGO SAY “CULINARY EXPERIENCES” ARE THEIR PRIMARY REASON FOR THE VISIT. THESE SITES WILL MAKE SURE THOSE EXPERIENCES ARE UNIQUE AND MEMORABLE.

Eater Chicago – If you’re looking for the scoop on Chicago dining, drinking, food and nightlife check this site out. If you’re local and haven’t heard of it then you’re going to have some fun for a few hours. If you’re visiting and want to get down to the nitty gritty here are the best features for you:

• Eater Chicago Essential 38 Restaurants (the answer to: “Can you recommend a restaurant?”
• Eater Chicago Heat map (hottest Chicago restaurants)
• We can’t link to this one, because it changes every weekend. But Eater Chicago has a feature every Friday & Saturday they present the best restaurants in Chicago with last minute reservations available from Open Table. Check it out when you’re in need of a place to eat but completely forgot to reserve your spot.

LTH Forum – This is a legit foodie website. It’s not flashy. It’s not sexy. It gets right down to business. The site is the work of Chicago locals who left another “more restrictive” food blog to start their own. Whether you want to meet up with locals to break bread together or you’re interested in getting the scoop on some neighborhood haunts – check this site out.

WEATHER AND TRANSPORTATION ARE TWO VERY UNPREDICTABLE ASPECTS OF CHICAGO LIFE. USE THESE SITES AND APP TO HELP YOU PLAN AND PREPARE FOR ANYTHING.

Spot Hero – For anyone that is going to be driving and parking in Chicago. This is the app for you. It’s almost too good to be true. You plug in where you need to park (an address, landmark, whatever) and the date range. Next thing you know it’s telling you all the spots – both public and private – that you can park at, their location and their price. That is it. Search for the spot, find the spot and pay for it.

RideScout – The all-in-one-whatever-mode-you-want-to-travel transit app has arrived to Chicago. Yay! This app will help you get from point A to point B. Whether you want to take a taxi, a bus, walk, bike, car share, park your care or whatever. All in one simple screen. This is great for those that want to take advantage of every single type of transportation possible in a city (you know who you are) and for those looking to take the most efficient route because they’re running late. Or for those that just want to see how close their friends can guess as to the time difference between taking a bike vs a ride share. Have fun.

Chicago Pedway – Wait, what’s a pedway? It’s a noun -a footway built for pedestrians in an urban area. In Chicago’s case it’s an underground pedway. But why you may ask? To help give you cover for our awful Chicago winters. Many locals don’t even know about it. Now you’re in-the-know. It’s sort of a tangled mess of underground walkways, but we have to admit it’s quite unique and if you have time (or for some reason you’re visiting in the winter) make sure you take a visit.

Dark Sky – Chicago is the Windy City. You have probably heard all of the silly one-liners. “If you don’t like the weather in Chicago, wait 15 minutes.” Chicago has four distinct seasons and then some. Cheers to Dark Sky and the technology behind it that can alert you down to the minute (not kidding) when it will rain or snow in Chicago.

CHICAGO ENTERTAINMENT. ENOUGH SAID.

Free Museum Passes from the Library – Sorry out-of-towners, this one is strictly for locals with a valid ID and Chicago address only. We just couldn’t leave it off our list though, it’s too good. This might even be the last drop in the bucket to motivate you to pack up and move to Chicago.

Just like the link says, if you have a Chicago Public Library card you can “check out” passes to the museum good for up to two adults. The catch? You MUST be accompanied by a child under the age of 18. And yes, the #1 Museum in the World is on the list.

ChicagoPlays – Remember those 200+ theaters that were mentioned in the opening paragraph? ChicagoPlays will make it much easier for you to navigate all that is happening in Chicago. Find a theatre. Find a play. Look by date. Look by what is hot. Buy Tickets. Have fun.

Did we miss a great site that needs to be added on this list? Let us know by adding your comment below.