Chicago, which sits on the shores of Lake Michigan, is famed for its bitter winters, deep-dish pizza, gangster history, skyscrapers and St. Patrick’s Day celebrations. It also happens to be a perfect long-weekend destination and an ideal rival to the more expensive New York getaway. From iconic views across the city at the top of the John Hancock Center or Willis Tower, to world class museums such as the Art Institute of Chicago, the Windy City has something for everyone. Read on to learn more about Chicago’s top tourist offerings and some top tips to maximize your stay.
Chicago Top Tips
Chicago has two major airports, Midway and O’Hare, and the easiest and quickest option to get to and from both is the L Train.
O’Hare is served by the Blue Line on the lower concourse of the terminal building and connects directly to Terminals 1, 2 and 3. If you’re heading to or from Terminal 5 then there’s a separate, free, shuttle train. The journey downtown to the Loop (see below) is about 45 minutes and costs $5 or less. When you compare that to a taxi fare of $40 and a potentially traffic-heavy journey of up to 90-minutes, it’s both efficient and a bargain!
Midway is served by the Orange Line, and the station is located just outside the terminal building (accessed under an enclosed walkway – which is nice when it’s pouring down with rain). It’ll take about 25 minutes to reach downtown and will cost you $2.50 or less. Compare that to up to 40 minutes in a taxi and a bill of about $25.
When I started researching Chicago, I saw constant references to ‘The Loop’. Having not previously visited, and with little in the articles I read explaining what it was, I had to look it up elsewhere. To avoid you having to do the same I thought I’d briefly explain what is actually very simple. The Loop is the neighborhood at the very center of downtown where 85% of the tourist attractions are and where you’ll be spending most of your time. Why is it called The Loop? Not so simple. The easiest answer is that the area is surrounded by the elevated tracks of the L Train (i.e. it creates a loop of tracks around the area). However, some historians claim that the term originated before the L Train existed and it refers to cable car system that no longer exists. So, in summary, who knows where the term really came from, but it’s where you’ll be spending most of your time.
Once you’re in town then most of the major attractions in the Loop are walkable. If you’re heading outside of the Loop, then you’re best to hop back on the L train or on a bus. If you do plan to use public transport a fair amount, then you might want to consider getting yourself a Ventra Card or ticket. If you buy these at the airport when you arrive, you’ll have the option of disposable 1 and 3-day tickets that give you unlimited rides. Alternatively, you can buy a Ventra Card which can be loaded with credit and can be used to cover fares for up to 7 people. You can read more about the Ventra options HERE.
Another purchase you might want to consider is one of the tourist cards on offer – particularly if you plan to visit a few different museums or pay-for attractions. Rather than bore you with al of the available options right here and now, I’ll just point you in the direction of the write-up on the Free Tours by Foot website, which provides a really useful breakdown of the options available.
Like all big cities, Chicago has a smattering of tour and hop-on-hop-off bus options. Whilst doing a deep-dive into all the options would be extremely boring, I will just quickly mention two of the main options available: Big Bus and the Chicago Trolley & Double Decker Co. Big Bus has all the usual benefits of a big international brand. You know exactly what you’re getting. The Chicago Trolley company offers much the same in terms of routes and stops (including offering night tours). I’d therefore suggest that you base your choice on any deals that might be available at the time, or if any combination of attractions can be bundled to get you a bargain. Alternatively, just use the much more cost-effective (and comprehensive) L Train twinned with a guidebook and save yourself some money!
If there’s one thing Chicago is famous for (besides deep-dish pizza, gangsters, hot dogs, and St. Patrick’s Day celebrations) it’s probably its weather. As it’s lovingly called the ‘Windy City’ you probably already know what to expect. But in addition to the lake-effect wind it’s also worth noting how bitterly cold it gets in the winter. So cold in fact that most tourists won’t even bother traveling to Chicago in the winter (not least because some of the city’s main tourist attractions all but shut down in the cold). But I’m of the opinion that Chicago in the winter has some definite advantages. Check out my article on why you should consider visiting Chicago in the Winter to learn more.
Architecture River Cruise and River Walk: After a massive fire in 1871 that destroyed 17,500 downtown buildings, Chicago took the opportunity to rebuild; and birthed the modern-day skyscraper in the process. It’s therefore no surprise that Chicago is acclaimed for its architectural heritage, and there’s no better way to explore it than on an architecture cruise along the Chicago River. The most famous of the cruises on offer is the Chicago Architecture Foundation Center river cruise aboard Chicago’s First Lady. And if architecture isn’t your thing then there are a host of other river and lake cruises on offer – everything from quick jaunts up the river to upscale evening cruises offering multi-course meals. You can check some of those out HERE. If you happen to be traveling to Chicago when the cruises shut down for the winter then make sure you consider one of the Architecture Foundations architecture walks instead.
Magnificent Mile: I think calling it ‘magnificent’ might be slight overkill, but if you’re looking to experience the center of Chicago’s world of shopping then this is probably it. A stroll along Michigan Avenue (that’s the road’s actual name) will also mean that you’ll stumble across the Old Water Tower, which is worthy of a photo stop and itself houses a range of local art and photography exhibits, the John Hancock Center (see below), and the original Gino’s East (also see below). If I was to summarize the Magnificent Mile then I’d say if you’re a shopping addict then it’s as good a place as any to get your fix, but I probably wouldn’t plan to dedicate much of your precious time here (admittedly, that’s coming from a man who hates shopping to his very core).
Navy Pier: Another of Chicago’s attractions that seems to appear on every ‘must-visit’ or ‘top-10’ list for Chicago that I’ve seen. To be honest, that’s really the only reason I’ve included it here (such a sheep). In reality, Navy Pier is little more than a nightmare scenario of tacky tourist ‘attractions’ all lumped together in one place (probably to keep the tourist masses out of the way of local Chicagoans trying to live a normal life). So, what exactly is there? Think I-Max theatres, carnival rides, chain restaurants and shopping. If you’re a cultural tourist, then the only reason you might want to stop by is to get a good view and a photo of the downtown skyline. However, if you’re traveling as a family then Navy Pier might just be the perfect place to keep the kids quiet for a few hours!
Museums: Wow. Where do I start? Chicago has one of the most impressive line-ups of museums anywhere in the World. I’d go as far as to say that if you visit for a weekend then you’re almost guaranteed to visit at least one. And if it is just one, then it should probably be the Chicago Institute of Art. The Institute is one of the oldest and largest museums in the US and has been consistently ranked as one of the best museums in the world. Home to over 30,000 works of art and a range of ever-rotating exhibitions, it’s an art lover’s paradise (my wife was in heaven). If art isn’t so much your thing (yeah, that characterizes me), then your alternative museum options include the Field Museum (essentially a natural history museum), the Museum of Science and Industry (where you can explore a full-size submarine), the Adler Planetarium, the Shedd Aquarium, the Museum of Contemporary Art, the Chicago History Museum, the Children’s Museum, the DuSable Museum of African American History, the Oriental Museum Institute, the Smart Museum of Art, the Museum of Contemporary Photography (more my scene) or the Chicago Cultural Center (worth visiting just to photograph the lobby!). For a full, mind-blowing, 117 museum options (at the time of writing) check out THIS list.
Sky High Views: Chicago is undoubtedly a skyscraper kinda city. It therefore shouldn’t come as much of a surprise that two of its major attractions come in the form of skyscraper observation decks. The first of these is the Skydeck at Willis Tower (probably better known by its former name, the Sears Tower). The Skydeck, which sits up on the 103rd floor of the tower is the home of ‘The Ledge’; where you’ll have the chance to step out on to a glass-floored balcony 1,353ft in the air. The Skydeck admission also includes access to an interactive exhibit about Chicago’s architecture. Tickets can be purchased HERE.
The second option is called 360 Chicago and can be found at 875 N Michigan (formerly known as the John Hancock Center). Like the Willis Tower’s Skydeck, 360 Chicago also has its own adrenaline-inducing attracting, TILT. Unlike the ledge, which you walk out on to, TILT offers the opportunity to be gradually lowered out over the city (but while remaining inside) at a 30-degree angle by hydraulic bars.
From everything I’d read in the run-up to our trip the views from 875 N Michigan are the better of the two. And seeing how I prefer a glass of whiskey over being hoisted mechanically off the side of a building, we opted for a third choice; Happy Hour at the Signature Lounge on the 96th floor of 875 N Michigan. The result was that I got the same views, for about the same price as the entry ticket, but I came away with a better buzz! I highly recommend this option out of the three.
Millennium Park: Other than taking an architecture cruise, visiting Millennium Park should probably be right at the top of your itinerary. The main reason for that is to get the obligatory picture of ‘Cloud Gate’; you know, that shiny, metallic, bean-looking piece of art that has become the symbol of Chicago and the focus of many an Instagram-selfie. But Millennium Park is more than just ‘the bean’. It’s the beating heart of the city, a great place to stand in awe of the Chicago skyline, a place to chill out in the summer as you watch a live performance, or to ice skate in the winter. The park is also home to the Crown Fountain; a reflecting pool flanked by a pair of 50ft towers mounted with LED displays showing artistic videos.
If you plan to photograph Cloud Gate or Crown Fountain, then I’d suggest a couple of things. First, make sure to visit twice, once during the day and once after dark. The skyline from the park is particularly impressive once the sun goes down and the city lights come on. Second, try to time your daytime visit as early in the morning as possible. That way you’ll get great pictures of Cloud Gate before most of the crowds arrive to spoil your shot.
Buckingham Fountain: 1.5 million gallons of water, nearly 200 jets reaching heights of up to 150ft, and an hourly show set to lights and music. The Buckingham Fountain in Grant’s Park has been a city centerpiece since it opened in 1927. Get here at dusk to watch one of the shows that start at the top of the hour, every hour between 9am and 10pm and you’ll be rewarded not only with a 20-minute light show, but also a great cityscape backdrop. If you’re planning to visit in the winter, then the bad news is that fountain only runs when the water won’t freeze (typically from early May until mid-October). But even without the show it’s still an impressive fountain and a great view of the city.
The 606: If you’ve ever visited New York, then you’ll know that one of the newer highlights is, at least in the summer months, taking a stroll along the ‘High Line’ – an abandoned, elevated, railway line that’s been converted into a park that meanders its way through downtown. Well, the 606 is Chicago’s version of the High Line. What was previously the Bloomingdale Line (which closed in the 1990’s) has now been converted into a public space that includes art installations, event spaces, and biking and running trails. Check out the 606 Website and interactive map to plan your visit and to see if there are any public events worth catching while your in town.
Lakefront Trail and Chicago Beaches: Chicago is blessed with 18 miles of Lake Michigan waterfront that, in the summer at least, provides an oasis from city life, a great place to stroll, bike, skate, swim, and sunbathe. Together with the Lakefront Trail the city also boasts a whopping 25 free public beaches. Arguably, the most popular of those beaches is North Avenue, located just north of the city. The beach offers plenty to keep you active if you arent a sun worshipper: bike rentals, wake and paddle boarding, jet skiing, kayaking, volleyball and, of course, swimming. If all that activity makes you thirsty then make sure to drop by Castaway’s Bar or relax in a waterfront cabana at Shore Club.
Food: I’m of the opinion that no guide to Chicago is truly complete without making mention of Chicago’s food scene. From it’s 22 Michelin starred restaurants to its hole-in-the-wall takeaways, Chicago has something to tickle everyone’s taste buds. But, putting haute cuisine to one side, there’s probably two things that immediately spring to mind when you think of Chicago: deep-dish pizza and hot dogs.
- Hot Dogs: If you’re looking for the one place everyone talks about, and don’t mind a bit of trek outside town, then you should visit Superdawg Drive-In for a truly authentic experience. But if you’re trapped downtown without a car, or don’t fancy making a hotdog run a significant portion of your weekend itinerary, then check out Downtown Dogs on Magnificent Mile.
- Pizza: Here’s where the real debate is: which pizza place does it best and who invented the deep-dish? Several places claim some sort of bragging rights over the dish, so why not just check out them all: Giordano’s, Pizzeria Uno, Pequod’s, Lou Malnati’s, or Gino’s East. We personally opted for the original Gino’s East on Magnificent Mile – mostly because the décor and ambience looked cool! It didn’t disappoint.
If you’re looking for somewhere with a few more options but that still showcases local food then make sure to check out the Revival Food Hall located in the heart of the Loop. This 24,000 square foot food market brings together some of Chicago’s best eateries under one roof in a grab-and-go style – making it the perfect spot to grab a bit for lunch.
Live Comedy: Another thing Chicago is famous for is its comedy scene; and nowhere is more famous for its improv sketch comedy than Second City. Second City alum include Tina Fey, Mike Myers, Steve Carell, Jordan Peele, John Candy, Bill Murray and a huge amount of other famous faces. So, it’s no wonder that a night out watching a Second City show is incredibly popular amongst visitors to Chicago. Tickets are available on their website, but if you’re looking for cut price deal then make sure to check out Hot Tix as tickets are often half price.
Chicago Transit Authority Website: https://www.transitchicago.com/visitors/
Ventra Pass Website: https://www.ventrachicago.com
Chicago Water Taxi Website: https://www.chicagowatertaxi.com/
Free Chicago Walking Tours Website: https://freechicagowalkingtours.com/
Big Bus Chicago Website: https://www.bigbustours.com/en/chicago/chicago-bus-tours/
Chicago Trolley & Double Decker Co Website: https://chicagotrolley.com/