How to make the most of your weekend in Chicago!
Have a free weekend coming up but aren’t sure what to do with it? Well, we strongly suggest that you fight the urge to laze away those precious days and consider a trip to Chicago. Why Chicago? Because we just got back from there ourselves and can give you all the tips you need to have a great time, of-course! In all seriousness though, Chicago is a weekend-reveler’s paradise with everything from ancient buildings and enormous modern skyscrapers to fine dining, museums, rooftop bars and even a Great Lake! Add in the fact that you can enjoy all these things on foot and with almost no advanced planning and you’ve yourself another perfect weekend getaway spot!
Getting to Chicago
Two airports serve the city of Chicago: O’Hare international and Chicago Midway International airports. Both are located approximately 30 minutes away from the city center by car and have plenty of availability when it comes to taxis and other ride-shares. On the surface, it appears that these airports are created equally however, there are some differences between them that are worth mentioning and that may influence your decision on where to fly. First, O’Hare International tends to have more frequent flights when compared to Midway International however flights seem to cost about the same at both airports. Second, even though the distance from each airport to downtown Chicago appears to be about the same when mapped, Midway Airport is, in fact, located a little bit closer to downtown Chicago than O’Hare Airport. Why is this important?
Because Chicago traffic can be a beast and can turn your 30-minute commute into a 2-hour ordeal so picking an airport closer to your destination just makes sense. Finally, even though both airports offer trains into the city for around $2.50, the are no direct trains from O’Hare airport and the commute time is about 45 minutes one way. Midway Airport, on the other hand, has a direct train (the orange line) that travels to downtown Chicago in just 20-25 minutes! So, which one is actually better? Although O’Hare is a perfectly good option, we would have to say that Midway Airport is the clear winner as it cuts down significantly on travel time thanks to its location, cost effectiveness and convenience. If only we knew all this before we booked!
Do you need a rental car?
We would have to say no for two main reasons. One, Chicago has many reliable and affordable options for public transportation. There are buses and trains operating to practically anywhere you might want to go. To simplify matters when it comes to using public transport, we recommend purchasing an Unlimited Ride Pass which cost just $5 for 24 hrs and which works for buses and trains. There are also 3-day, 7-day and 30-day passes available. Check prices here. If you’re on a time crunch, ride-shares like Uber and Lyft are readily available as are city taxis in the downtown area and tend to have reasonable fares. The following may be somewhat counterintuitive advice in the current era of flexible pricing ride-shares, but we have to encourage you to take at least one taxi ride in the city. The reason we urge you to do this is that being audience to the skills of the local taxi drivers in smoothly navigating the dense traffic is truly entertaining and a one-of-a-kind experience. We don’t think we’ve seen driving so skillful yet not terrifying anywhere else in the world. Honestly, if you need to get someplace quickly, we think you’d be much better off with a taxi than a rideshare but we digress.
Two, parking can be difficult and costly in downtown Chicago. Add in the price of the rental car itself and you’ll notice that the cost of having a car for a short weekend getaway far exceeds the cost of using public transportation or ride-shares. We should point out that downtown Chicago is very walkable so don’t be afraid to load up your maps app and just go for it. And, if walking long distances isn’t for you, there are also plenty of scooters and Lyft bikes available for rental. Just grab any available bike and cruise down Michigan Avenue, the Riverwalk or anyplace you fancy!
Where to stay?
If you know anything at all about Chicago, then you most likely have heard of the Loop and Magnificent or “Mag” Mile. But what are these places? Well, the Loop is, in fact, a 35-block section of downtown Chicago that is defined by the “El” train that forms a Loop around this section of the city. There are actually three “Loop” neighborhoods with these being The Loop itself along with two other adjacent neighborhoods known as South Loop and West Loop. The three Loop neighborhoods are densely populated, offer much in the way of entertainment and food and are fairly close to each other and Lake Michigan. Hopefully, you’re following us so far but a question still remains: What’s Magnificent Mile and is it in any of the Loop neighborhoods?
Mag Mile, interestingly, is not within any of the Loop neighborhoods. It is, in fact, a 13-block section of Michigan Avenue just adjacent to the Loop that connects the Gold Coast and The Loop. Mag Mile’s claim to fame is its high-end shopping, luxury hotels, abundant restaurants and hopping night life. So, why is all this important? Well, knowing what these neighborhoods are is the first step to finding the perfect base to explore Chicago on your weekend getaway. With limited time on hand, we’re sure you don’t want to waste any of it on unnecessary commuting, right?
We would argue that it’s hard to go wrong in any of these areas but if you’re looking to do a lot in a short time like we were, we highly recommend staying on Mag Mile. We stayed at the Westin on Michigan Avenue and were incredibly close to tons of food, the Oak Street Beach, the Old Chicago Water Tower and lots more. We were also within a 10-minute drive or 30-minute walk of other famous Chicago attractions like the bean and Navy Pier. Some of our party stayed in South Loop and had slightly less access to night life and restaurants but were within walking distance of things like the Field Museum and the Adler planetarium. All this to say, just pick a hotel that looks comfortable to you in either The Loop, South Loop, West Loop, or Mag Mile and prepare for an awesome time.
What's the weather like?
Well, this pretty much depends on the season. Want to experience a day in the life of a popsicle? Then visit Chicago in the winter! If you didn’t already know, Chicago winters are harsh with brutally cold temperatures and wind so numbingly cold that it can probably penetrate the 15 layers of clothing you’re planning to wear to fight off hypothermia. Fall and Spring experience milder days but, thanks to the ever-present wind, these seasons can also be chilly.
If you’re looking for those idyllic days with warm, sunny weather and gentle breezes then make sure to visit in the Summer. In fact, we suggest that you go ahead and plan your visit during the Summer as this is when the city of Chicago comes to life and regains its vibrancy. Not only can you freely explore the city without having to bundle up, you can also take advantage of the many free outdoor events and concerts! We do have to point out that while temperatures are usually pleasant in the summer, it’s not unheard of to have summer days with temperatures in the 90s-100s. Don’t worry too much about this though as it is not a very common occurrence. The idyllic Goldilocks, meaning not-too-hot-not-too-cold, summer days make Chicago a great getaway spot especially if you’re tired of melting in the summer heat of your own hometown. Oh, and let’s not forget to mention that, as this is the Windy City, having a light jacket at the ready for those days when the wind really kicks up could prove to be very handy!
What to eat?
Chicago’s most famous dishes are undoubtedly the Chicago-style Hot Dog and the Chicago-style deep-dish pizza and, no matter how you may feel about these particular foods, you HAVE to try both when you visit the city. If you choose not to then know that you risk the wrath of Chicagoans everywhere! Nah—we’re just kidding. Chicagoans would probably thank you if you decided not to try these dishes as it means more for them! But you would be missing out on some very interesting takes on these classic dishes.
A Chicago-style hotdog is much more formidable than a traditional hotdog. Made with a large, all-beef hotdog nestled in a poppy seed bun and topped with onions, sweet relish, sports peppers, slices of tomato, an entire dill pickle spear and just the right amount of mustard, this hotdog is essentially an entire meal in 4 bites. We recommend checking out Portillo’s and Barnelli’s for an incredible rendition of this hotdog. And make sure not to offend anyone by asking for ketchup!
Chicago-style Pizza, like the Chicago-style hotdog, is quite extravagant. What do we mean by this? Well, call to mind a regular slice of pizza—now multiply the thickness of the crust by a factor of 10-15 and, voilà, you’ve got yourself a deep-dish pizza. Of course, there’s more to it than that! To be a true Chicago-style pizza, the pie must be assembled crust first followed by cheese and other toppings then topped with sauce. All of this bake together to create a thick, gooey, pizza. We sampled deep-dish pizza from Lou Malnati’s and Art of Pizza. The pizza from Lou Malnati’s was fresher but Art of Pizza had a better-tasting sauce. Unfortunately, we discovered that we were not fans of this style of pizza having been inducted into the cult of New York-style Pizza Lovers Only although this does not mean that these pies weren’t tasty. In fact, we thought the pies tasted good but that the crust was blasphemous. Anyway, how we feel about it doesn’t really matter though as you just need to have a slice and decide how you feel about it! You may love it…you never know!
Aside from these two must-try dishes, there are tons of restaurants to choose from in downtown Chicago ranging from top-notch fast food to Michelin star fine dining venues. Some honorable mentions in the fast-food category are the spicy fried chicken from Jollibee and the Italian beef sandwich with extra gravy from Portillo’s both of which are to-die-for! We also enjoyed the perfectly balanced and savory chicken tikka pizza from Himalayan Curries and Pizza as well as their crunchy masala fries. As far as upscale dining goes, we thought the Peruvian roasted chicken from Tanta was juicy, super tender and well-flavored. Our favorite cocktail of the trip was the Pisco Sour, also from Tanta!
What to do in Chicago?
Even if you’re on a time crunch and don’t think you’ll be able to get as much sightseeing in as you’d like to, don’t fret! If we can visit two thirds of the major attractions in just one day, you can definitely get to most of it over a single weekend. Thanks to the proximity of the attractions to each other and the general ease with which the city can be navigated, it’s likely that you’ll be able to see just about everything you have your heart set on! Here are some of our favorite attractions and where they’re located as well as some recommended things to do to help you plan your trip.
Adler Planetarium
Located on the tip of Northerly Island and easily accessible from South Loop, the Adler Planetarium is not just any planetarium. Sure, the inside is much like others and is mostly dedicated to astronomy and astrophysics with plenty of mind-bending visual spectacles however the outside really sets it apart. The planetarium building itself faces out towards the blue-green waters of Lake Michigan while the meticulously maintained grounds provide unparalleled views of the Chicago skyline across the lake. Once there, don’t forget to check out the adjoining Doane Observatory which houses the largest telescope available for public use in Chicago.
Northerly Island
Although Adler Planetarium may captivate you, don’t forget to check out Northerly Island itself. Just south of the planetarium is a meandering path with spectacular lake views that leads to the 12th Street Beach. While we were skeptical that any of the beaches would be enjoyable given the wind and subsequent waves, we were pleasantly surprised by this beach. With wave breaks at the entrance to the cove-like beach, the waters were calm enough to swim and pleasantly warm to boot! We recommend that you bring along a swimsuit and let this gorgeous Lake Michigan beach soothe away your troubles!
If you’re not quite ready to hit the beach, then check out the outdoor art installations at Daphne Garden or take a hike through Northerly Island Park. Honestly, with so much to do so close together, you could spend an entire day just taking in Northerly Island.
Field Museum
Positioned at the entrance of the main thoroughfare leading to Adler Planetarium, and still within South Loop, is a park consisting of several notable attractions one of which is Field Museum. In our opinion, this is one of the absolute best things we did in Chicago! Not that we’re connoisseurs when it comes to what makes a museum great, but we were struck by the sheer volume of exhibits and how well-structured, informative yet engaging the entire museum was. We purchased an all-inclusive pass for $43 per person which gave us access to all the exhibits, an informative and engaging 3-D dinosaur movie, and four additional special exhibits. We spent almost three hours in the museum and still wanted more time to thoroughly take in everything! We won’t give away too much but if you’re into Dinosaurs, natural history and rare collections from practically every continent, then you have to add this place to your must-see list.
Soldier Field and Children’s Garden
Just across the street from Field Museum is the Soldier Field Children’s Garden and Soldier Field stadium. Plan to catch a game at the historic stadium if you’re in town at just the right time. Don’t forget to grab a picture at the Eternal Flame of Hope on your way across the street to Soldier Field!
Shedd Aquarium
While we did not get a chance to visit the aquarium ourselves, we wanted to point it out to you as it’s located within a less than 5-minute walk from Field Museum and Soldier Park. Had we known of its proximity to our stomping ground we would’ve most certainly paid a visit however our loss is hopefully your gain! The Aquarium sits on the banks of Lake Michigan, and we can only imagine the spectacular views from within. Definitely don’t miss your chance to check out this awesome spot.
Buckingham Fountain
Formally known as the Clarence F. Buckingham memorial fountain, this decidedly unique fountain is also one of the largest fountains in the world. Located within Grant Park, the fountain is about 1 mile North of Adler Planetarium and is reachable by a 10-minute car ride or a 20-minute walk. Why make the effort? Unlike other ordinary fountains, this one is interactive and has major water displays for 20 minutes every hour beginning at 9am daily. The shows continue until 10pm and, when it gets dark, also includes eye-catching light displays too. Plus, if you get tired from the walk, there are plenty of benches to sit and take in the show while you enjoy ice-cream or cotton candy from the nearby street vendors!
Millennium Park and The Bean
Once you’ve taken a much-needed break at the fountain, especially if you’re doing all of this in one day, head North towards Millennium Park. This route will take you through the lush North Rose Gardens where you can capture a picture with the Crane Girl sculpture. Continue walking further North from this point to take in Butler Field and the Maggie Daley Park. If you’ve got kids in your party or just want to get in touch with your inner child while freaking out parents, head over to the Play Garden. In all seriousness though, the play garden is 3-acres of fun space for everyone to enjoy that does have some age-specific areas. While most of the activities are engineered for children, adults can also enjoy the splash pad, walk the enchanted forest or just chill-out on the swings.
After the probably much-needed interlude at the playground, head across the street, finally, to Millennium Park. As you make your way through the park, you can check out Lurie Garden or the Crown Fountain. One sight you definitely don’t want to miss in the park is Cloud Gate which is more commonly known as The Bean. The Bean is a huge, reflective art installation in Millennium Park that is a great spot for photo ops. The surface of the sculpture is so reflective that the Chicago skyline can be clearly seen on its surface! Finally, be sure to see if there are any free concerts happening while you’re in the park, you don’t want to miss out on the cool tribute bands that pass through the park in the summer!
The Riverwalk
Taking the Lakefront Trail, which is located across the street from Buckingham Fountain, make your way along one of the most scenic pedestrian routes from the shores of Lake Michigan to the Chicago River Walk. The Lakefront Trail appears to simply end where the Riverwalk begins so there’s no need for excessive planning. Just make sure that you’re following the trail North and away from Adler Planetarium. Open daily from 6am to 11pm, the Chicago Riverwalk is a one and a quarter mile stretch extending westward away from Lake Michigan and toward the DuSable Bridge. The walk is pretty, well-kept, and lively and is an ideal hangout area thanks to the many restaurants, bars, lounges and endless emerald water views. We should also point out that the Riverwalk is an excellent launching point for kayaking and other watersports if you feel like seeing the city from a different vantage point.
Navy Pier
Even further North of Millennium Park and Adler Planetarium and closer to Magnificent Mile is Navy Pier. Navy Pier is quite like a carnival albeit a much cleaner and more sophisticated one. The pier boasts cruises, concert venues, restaurants, and rides like the iconic Centennial Wheel. If you’re visiting on a Saturday in the Summer, we recommend making an evening of it by grabbing a bite to eat then catching the incredible 10pm fireworks show.
Willis Tower
The Willis Tower is a 110-story skyscraper located within the Loop. Interested in a bird’s eye view of Chicago and Lake Michigan from the tallest building in Chicago? Want to walk out onto a glass balcony extending 4 feet outside the 103rd floor of the tower? If you’re not afraid of heights, then make your way to the Willis Tower to catch tremendous views and to experience The Ledge. Make sure to buy tickets here.
Local tip: If you don’t want to go as high as the Willis Tower but would like to catch a great overhead view, we recommend heading to the John Hancock Building. You’ll notice signs to 360 Chicago which is a tilting observation deck and a pretty cool experience in itself. The cost of a ticket is about $30 per person just to see the view which is a little steep if you plan to only spend a short time there. Instead, we suggest heading up to the lounge area of The Signature Room at the 95th then taking a detour to the lady’s restroom. The floor to ceiling windows in this particular bathroom provides a breathtaking, panoramic view of downtown Chicago and Lake Michigan. It’s free to enter the building and visit the lounge so you can take all the insta photos you need without paying a penny! All credit for this incredible find goes to our friend and former Loop Local, Anu, without whom we would never find this amazing view!
Plaza of Americas/DuSable Bridge/Chicago Water Tower
Fortuitously, our impromptu walk from our hotel on Mag Mile to the Chicago Architectural Center (CAC) took us past several ornate, historical buildings including the Chicago Water Tower. The Chicago Water Tower is one of only a few buildings to survive the Great Chicago fire in 1871 and is a truly one-of-a-kind landmark. As we continued West, we came upon the Plaza of Americas and the sculpture of Benito Juarez. We stopped to admire the golden “Wings of Mexico” art installation but, regretfully, did not get our own winged pictures! With that small disappointment behind quickly forgotten though, we resumed our walk to the CAC but stopped short once again as we took in the magnificent DuSable Bridge. Words don’t really do justice to this jaw-dropping feat of architecture and the splendor of its four enormous bridge houses so check out our pictures, or better yet, add it to your to-do Chicago list and see it for yourself!
Chicago Architectural Center (CAC)
We didn’t necessarily aim to visit the Chicago Architectural Center (CAC) however our hotel stay included complimentary tickets which we decided to make use of. As you can see above, we’re extremely glad we made the 30-minute walk from our hotel across the Chicago River via the DuSable bridge to get there! Even though the walk may seem a little long, we still recommend doing it if you’re able as there’s no better way to enjoy the incredible beauty of the city. The CAC is perhaps exactly as you might imagine: a place to envision buildings of the future. We enjoyed touring the conceptual designs and learning about more eco-friendly building materials and techniques. It was also fun matching the buildings along the Chicago River with the guide provided by the CAC. A little nerdy we know but what can we say, we are who we are! Regardless of whether you’re into what the CAC has to offer this particular area of the city is absolutely splendid and should be high on your sightseeing list!
