- Airport – O’Hare International (ORD), Midway International (MDW)
- Currency – U.S. Dollar ($)
- Language – English
- Chicago Population – 2.7 million
It is hopeless for the occasional visitor to try to keep up with Chicago. She outgrows his prophecies faster than he can make them.
-Mark Twain, 1883
Chicago was ideally situated to take advantage of the trading possibilities created by the nation’s westward expansion, utilizing access to both the Great Lakes and the expanding railroads. Today, 50% of all U.S. freight rail still passes through the city. The city is also well known for the Great Fire of 1871, which left over 100,000 residents homeless. Chicago remained resilient, however, and rebuilt nearly the entire city over the next 20 years.
Chicago is the birthplace of the refrigerated rail car (Swift), mail-order retailing (Sears), the car radio (Motorola), the TV remote control (Zenith) and the nation’s first skyscraper (Home Insurance Building)! Chicago is an architect’s dream. It’s really known for architecture, and many of the nation’s best architects have ties to Chicago. The 1,450-foot Sears (now known as Willis) Tower, was completed in 1974 and is currently the second tallest building in North America.
Read Related Posts:
Chicago is a fantastic destination because of the cheap flights available from the U.S. coasts as well as it’s accessibility by car if you’re nearby! For housing, you can easily find a hotel or apartment on Airbnb downtown. Airbnb is definitely the most cost effective option for Chicago, especially if you’re planning a fun long weekend trip. You can take the Metra commuter train into downtown if you stay in the outskirts and walk around the city, or you can take Ubers around!
- Summer months
- Bring light summer clothes, comfortable walking shoes and sunscreen. It gets hot and humid!
- Winter months
- Pack your layers, a warm winter coat, gloves and a scarf. I would recommend going to indoor attractions like museums in the winter months with the snow and heavy winds.
- Year Round
- No matter what time of year you visit be sure to bring your camera and a pair of comfortable walking shoes! There are lots of great buildings and sights that you will want to remember, so have your phone or camera ready.
Wow! So many landmarks in this park. Built on top of the rubble left from the Great Chicago Fire, this is a great place to see the skyline and the iconic “Bean” (Cloud Gate). Be sure to take lots of pictures here! Other photo worthy attractions are:
- The Lions at the Art Institute – these lions are over 100 years old!
- Crown Fountain – get misted or soaked to cool off on a hot day
- Jay Pritzker Pavilion – awesome “basket weave” art installation makes this outdoor concert venue notable. If you’re there in Summer you may also see a group fitness class on the lawn!
- Buckingham Fountain – breathtaking, one of the largest fountains in the world
- Festivals – In the summer months, you may catch a free festival in the grassy areas of the park. We checked out the Jazz festival and relaxed in the grass to cool down while jamming out.
Explore Neighborhoods like Wicker Park and Old Town
Just outside downtown Chicago is Wicker Park, a neighborhood known for its creative flair. Come here to explore art galleries, enjoy live music, and sip on a coffee or cocktail in any of the numerous trendy cafés and bars in this area. For those who have been to New York, you could say that Wicker Park/Logan Square is like Chicago’s Brooklyn. You can take the blue line to the Damen stop to get to Wicker Park.
Another recommendation is to visit Old Town. This historic neighborhood is home to a myriad of individuals, making it a lively and colorful spot in Chicago. With Victorian buildings, brick alleyways and bright green trees, Old Town is all but too charming. Definitely also check out the Second City and Zanies Comedy Club when you’re feeling in the mood for some chuckles.
Walk Along the Chicago River
The Chicago River flows through downtown Chicago and has a rich history. It used to be a passageway for commercial activity but has since become a place for more recreational uses such as boating and kayaking. Walking along the Chicago River, you’ll see many cafés and small restaurants where you can sit down and enjoy the view. If you come to Chicago around St. Patrick’s Day, you’ll bear witness to the 50-year-old tradition of dying the river green.
Chicago Architecture Foundation Boat Tour
For a more educational experience of part of the city, consider taking the Chicago Architecture Foundation Boat Tour, which has been noted as one of the top 10 tours in the country. During this 90-minute boat tour, you are introduced to over 50 buildings along the Chicago River and the many stories that come with them. You can opt for the $44 daytime cruise, or the $46 twilight cruise, which begins at 7:30 p.m.
Check Out the Beaches in the Summer
Summertime in the windy city tends to be just as extreme as the wintertime. And what do you do when it’s hot out? You go to the beach! Chicago has a number of places for you to wiggle your feet in the warm sand and take a dip in cool waters.
- North Avenue Beach – located in Lincoln Park, this is one of Chicago’s most popular beaches. This place offers various activities, from beach volleyball to jet skis.
- Montrose Beach – if you’re a fellow dog-lover such as myself, head uptown to Montrose Beach. There’s a fenced-off dog area for furry friends to run around freely. For two-legged visitors, you can entertain yourself with activities like beach volleyball or kayaking.
- Oak Street Beach – You can also check out Oak Street Beach where many boats will anchor and party. Oak Street Beach is also closer to downtown. It’s smaller than North Ave Beach but still fun.
Visit The Bean!
Ah, the ultimate trademark of Chicago, Illinois. “The Bean” is actually just a nickname; this notable sculpture is actually named “Cloud Gate” because of the stunning reflection it gives off of the Chicago skyline. The Bean is located in Millennium Park of downtown Chicago, which is a very tourist-friendly place. While the Bean is always open, it’s best to go on a weekday when it’s a little quieter and less busy. Very Instagram-worthy!
Check out a Street Festival
One of my (and most Chicagoans) favorite things about summer is the festivals that happen on the streets of many neighborhoods throughout the city. Pretty much every summer weekend has a few different festivals where they close off multiple blocks, legalize alcohol in these areas, sell food, and have concerts. It’s pretty unique to Chicago and encompasses the city’s culture a little more than some of the typical tourist activities. There are also a bunch of ticketed music festivals, and the free blues festival in the park, but the music fests are not the same as the street festivals.
History, bars, more bars, pizza! If you want to go out while in downtown and watch sports, look no further than Wrigleyville. This cool, artsy area is a combination of old brick homes, historic bars & restaurants. The most interesting thing we saw were the makeshift stands on top of various apartment buildings – so you can watch the game without actually going in the field – tickets in these stands aren’t cheap though! There are also a ton of bars, some t-shirt stores with Chicago and Cubs gear as well. Wrigley Field offers tours for $25, but we just walked around the perimeter and looked at the iconic statues Next time we’re in town, we’ll plan ahead and buy Cubs tickets. My favorite place was Dimo’s Pizza, more on that below!
Visit the Adler Planetarium for its Monthly ‘Adler after Dark’
The Adler Planetarium has these amazing once monthly events called Adler After Dark. It’s always on a Thursday, and it’s a themed (ie. Back to the Future, Star Wars, etc — some people dress up in costume) ticketed event where you have unlimited access to all planetarium shows and exhibits. They serve booze, food, and have a dance floor, and it’s a 21+ event. They also have interactive activities and what not. It requires planning ahead because of the tickets, but it’s totally worth it.
Shedd Aquarium is also pretty cool. Both of these places are located on a peninsula type thing south of the city near Soldier Field and have amazing panoramas of the city – some of the best views.
Food in Chicago
Chicago is one of the best foodie cities in the U.S., and has something for everyone. Most famously are the hot dogs & deep dish pizza! Chicago boasts over 40 Beard Award-winning chefs and restaurants, second only to New York, the Beard Foundation awards restaurants for excellence in cuisine. While you’re there be sure to check out the West Loop, where you’ll find cool restaurants and bars as well
Chicago is also famous for American fare like steaks. Gibson’s Bar & Steakhouse is a major Chicago steakhouse institution Also, most Chicagoans will tell you that you need to try the local deep dish pizza. It’s pretty much mandatory to mention Lou Malnati’s – it is the go-to for deep dish and where most locals will tell people to go. Some people prefer Giordano’s but I think Lou Malnati’s is way better.
Garrett Popcorn Shops
A unique Chicago staple, their signature “Garrett Mix” is a combo of CaramelCrisp and CheeseCorn! They combine nuts with their caramel corn to make a sweet & savory snack – definitely worth getting a bag to keep in your room for the late night munchies!
Upscale decor and great service will make you feel like you’re dining in luxury – at a very affordable price. They have homemade smoothies (which you can get spiked) and almost everything they make is handmade – including the butter and syrup! This is a good spot for brunch on a Saturday or Sunday, but be sure to arrive early as it will be busy! We were able to snag seats at the bar and watch dozens of smoothies being made on a busy Saturday morning. Despite the hectic environment, we still had an attentive server, and the food was awesome as well – dairy free & vegan options were available.
“Alinea”, which means the beginning of a new train of thought — is a three star Michelin restaurant, run by its head chef and owner, Grant Achatz. As of June 2016, Alinea is ranked 15th on the World’s 50 Best Restaurants 2016. Alinea is about much more than just food. Alinea is an unforgettable food experience that will shatter any preconceived notions of how food should be eaten. Achatz takes such a creative and artistic approach to food, making the Alinea experience unlike anything you’ve ever experienced before. The meal consists of 18-22 courses, and with a wine pairing can cost around $500 a plate. It can take months to get a reservation at Alinea, so make sure to reserve your spot in preparation for your visit to Chicago.
Hands down one of my favorite restaurants I’ve ever been to, Avec is a must if you’re visiting Chicago. Avec is a shared plates restaurant and offers communal seating. The restaurant has the feel of a wine bar, with a special focus on wines from France, Italy, Spain, and Portugal. Avec is known for an always changing menu, as well as a few staples that you just should not miss out on. Make sure to try the Chorizo-Stuffed Medjool Dates and the Focaccia. Finish with the Cocoa Crunchies, a dessert that embodies an amazing balance of sweet and savory and is sure to satisfy.
Let me start by saying, every bite of this meal was enjoyable. From the amuse bouche to dessert, each bite was a whole new flavor experience. The restaurant itself is quaint and quirky at the same time, and all the food was cooked to perfection. Boka is a Michelin starred restaurant, and won restaurant of the year in 2015. The menu is seasonal, but anything you order will be delicious. Don’t skip out on dessert, Boka’s pastry chef, Meg Galus, was just recently awarded Pastry Chef of the Year in 2016.
The Purple Pig
A tapas restaurant located right on the Magnificent Mile, The Purple Pig is a great spot for adventurous eaters to grab lunch or dinner. The menu has a variety of unique options and combinations. The Broccoli with roasted garlic, toasted breadcrumbs, and anchovy vinaigrette was delicious, as was the Spanish Octopus and Fried Manchego cheese. In addition to its amazing food, The Purple Pig carries an extensive wine list and is the perfect place to go with friends.
The best burger I’ve ever had. If you are a burger connoisseur, you must try this place. Go early around 11 am because it fills up fast. Lunchtime is always packed and there is limited seating available. Make sure to order a Cheeseburger with bacon and a fried egg, and get ready for your life to change. This burger is unreal and lives up to the hype. Au Cheval is also known for their fried Bologna Sandwich, a twist on the classic school lunch.
New York style pizza in Chicago?! You might think I’m crazy, but this place is a must. Their motto is: “Eat Offbeat. Live Offbeat.” Located in Wrigleyville this would be a great place to grab a slice as you’re walking to the game, or stop in for a whole pizza if you have time – it only takes 15 minutes after all. They have unique recipes ranging from Chicken n’ Waffles to S’mores; bonus they have dairy free and vegan options too! There’s definitely a custom creation for anyone at this local hangout. We got half Vegan Buff Chick & Half Vegan Mac N’ Cheeze – so delicious & pictured below.
When you’re in the mood for some good old-fashioned, hearty, American BBQ, you need to come here. Heck, even when you’re not in the mood for BBQ but can’t decide where to go, try out Smoque BBQ! A no-brainer Chicago favorite, this place is packed most of the time and you’ll probably have to wait to be seated (go at an unpopular meal time to avoid this), but it’s well worth it. As for recommendations, you can’t go wrong with their St. Louis ribs or the Mac and Cheese!
The only way to describe this place is that it’s an experience, and most certainly not your typical lounge. If you watch Chef’s Table on Netflix, then you may be familiar with the chef, Grant Achatz, who is the owner of this remarkable cocktail bar. That being said, it is pretty pricey, but if you’re looking for a one-of-a-kind drinking experience, this is the place to go. I’m talking about interactive drinks, like changing colors, liquid nitrogen pouring onto the table, even having to literally use a slingshot to crack open your drink that’s trapped in a ball of ice. It’s pretty much entertainment that happens to be something you can drink!
The Violet Hour
For good cocktails and a speakeasy ambiance, check out The Violet Hour in Wicker Park. Just make sure you find the camouflaged door to enter.
GreenRiver has good cocktails and a cool outdoor patio on the 18th floor of 259 East Erie Street downtown. Sit at the bar and watch the scientific bartenders prepare your drink!
Signature Lounge: Have Cocktails at the Top of the Hancock Tower
A drink with a view. Signature Lounge is on the 96th floor of the Hancock Tower (one floor above Signature Room in case you’d rather dine with a view), so naturally you can expect a spectacular panorama of the city. As long as you order a drink, going up to the top of the tower will cost you nothing, and you can sit down, relax, and admire Chicago from above. I’d recommend going a little before sunset for the best visual experience. It’s a great way to start the evening.
A bit off the beaten path, but if you plan on taking the Metra, this is a good pit stop. Located inside Union Station this casual sports bar has reasonably priced drinks to cool off with before catching your train. It’s a local stop for those who just got off work, but they host game watching events as well!
See a Blues Music or Comedy Show
Blues music and stand-up/improv comedy are great in Chicago, which is one of the birthplaces for both. There are a few blues clubs — I’ve been to Blue Chicago downtown, but the real hub is supposed to be Kingston Mines. Live blues from local or better-known musicians every night. As for comedy, Second City is great, and you can experience one of Chicago’s proudest institutions.