The ultimate weekend getaway to Chicago: Best things to see and do.

Let’s say ‘hi’ to Chicago! Known as the Windy City, Chicago will literally blow your mind away, girl! This naturally breezy city is situated on the shores of Lake Michigan in Illinois, USA. I was super lucky to spend some additional days in Chicago downtown after some business meetings. Chicago comes prefect with the offers of relaxed beach life, marvellous city sights, iconic theater atmosphere and so many more things to explore and see. Chicago makes a perfect weekend getaway for your next solo trip: If you’re more the active one or looking for a great time off, you’ll both find inspirations for your trip alone or with your travel besties to Chicago on the weekend.

// General information for your weekend getaway to Chicago.

Arrival and transportation. Chicago O’Hare International Airport (ORD) welcomes both domestic and international flights. Closer to the city center is Chicago Midway International Airport (MDW), mostly prominent for domestic arrivals. To go to downtown, you can hop on the Blue Line ‘L’ train from O’Hare in about 45 minutes ($5.00) or grab an Uber for the next 30-40 minutes ($35.00). Arriving at Midway, the Orange Train Line will take you in about 20-25 minutes ($2.50) to central Chicago, an Uber will take 20 minutes ($25.00) for this route. In central Chicago, you can easily take public transportation or call an Uber. Please note, Chicago has tremendous rush hours, so better avoid 4.30-6.30 pm on weekdays for transportation matters.

Accommodation. It’s highly recommended to stay in the city center. You can go exploring right away, enjoy all sights within a short walking distance and staying right next to your night activities will make it for sure easy to fall asleep while still thinking about the greatest cocktails you’ve ever had, babe. Recommended areas for your stay is in Chicago Loop area and at Magnificent Mile. In these downtown neighborhoods you’ll find posh hotels, eclectic eateries, and the vibrant city life with an ultimate touch of theatre feeling.

Best time to visit. Chicago is definitely worth a visit around the year! However, in summertime your outdoor experiences are amazing – walk through the city while the sun kisses your skin, dine outside, and enjoy the beach. Winter is often freezing cold, but a really cool and unique winter activity will await you (see further down). There are always great things to explore in Chicago year-round, so don’t panic.

Note: COVID-19 pandemic might affect the activities described below. They might get cancelled or do not take place at your time of visit. Please check the providers’ pages carefully and regularly as things might change on short notice. Besides, the USA might close borders for tourists. Check out the government’s website from your home country for the latest immigration updates that apply to you.

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// Your weekend activities in Chicago.

For active ones.

My no.1 recommendation is exploring this incredible city by foot and a nice walk. You can start at the river walk area next to Wells Street Bridge. Continue walking on Chicago Riverwalk until you reach the harbor and Lake Michigan. Make a stop at the beach or Navy Pier. Continue your walk further down south to Millennium Park (Cloud Gate sight) and Grant Park (Buckingham Fountain sight). Walk over to the Chicago Theatre District and then back to the riverfront where you’ve just started. You can enrich this route with any of the activities described in the chapters below, girl.

Instead of walking, Chicago allows you to get explored on great routes for running. What about exploring the city through your daily run? You can run along the lakefront from Oak Street Beach to Millennium Park and Grant Park on the beautiful Lakefront Trail. If you are more into cycling, you can do that from North to South, too. The ways are mostly flat and easy to do. Several vendors offer bike rentals.

Are you in for some beach actions? North Avenue Beach offers great things to do. You can rent kayaks, jetskis, or can participate in yoga classes directly hosted on the beach. Of course, you can go swimming in Lake Michigan. There are various beaches with direct access to the lake on the lakefront.

Now it’s time for some super special events in winter. As mentioned, winters in Chicago can be extremely cold and snowstorms will guide the days. Chicago offers great ice rinks to enjoy the winter season. At the Ice Skating Ribbon at Maggie Daley Park you can skate a whole round of about one-quarter mile and can view the Chicago skyline from different perspectives in the background. They are unfortunately closed at the moment but will open their new season in winter 2021. Additionally, they request you to book time slots in advance. Entrance fee is cheaper when you bring your own skates. Second great option is the Ice Rink at Millennium Park. There you can ice skate directly in front of the famous Cloud Gate. Usually, the admission is free, you just have to pay a rental fee for skates.

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For food lovers.

Chicago is definitely famous for food. In more than 10,000 restaurants, food trucks, and shops, you’ll absolutely find your perfect place to eat. Let’s start your day right with a brunch. If you are in for something sweet or a healthy version, it is all ready for you. Check out the latest brunch options (even during the pandemic) with Eater Chicago.

It’s time for a sweet snack during your weekend getaway to Chicago. You’ve never heard about BomboBar? Now you know it. BomboBar offers rich hot chocolate deserts. I would say, it’s everything, hot chocolate, donut, cookie, whipped cream, ice, and so much more. It’s located in the West Loop and has a freaky menu for you. Also check out their instagram account to see their latest new crazy creations.

One of my favorite spots to dine out is along the Chicago Riverwalk. The restaurants that are located there offer great food and outdoor dining facilities. What about spending a great dinner with a perfect view over the river and the incredible Chicago skyline (when it gets dark outside, the skyline will start to sparkle). As I am a huge fan of seafood (especially mussels) with a river view, I found a really nice place to get them and dine outside: The Kitchen American Bistro. Of course, they offer other great dishes apart from seafood. Also a great pick is River Roast on the same side of the river.

When you’ll pass the river from Chicago Loop to the West Loop, another foodie paradise will await you. Located all around West Randolph Street, you’ll find nice eclectic eateries. If you are in for some French or Italien Food, or prefer a traditional American Steakhouse, they will have it all. Check out Eater Chicago for more iconic dining spots in the West Loop. They will also let you know about new openings at your time of visit.

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For night owls.

After a great day of sightseeing and impressions, get your nightlife started right, babe! I am a huge fan of rooftop bars. You can go outdoors – even better. First pick is the London House Rooftop Bar, located, exactly, on iconic London House building. It comes with amazing views over the Chicago river, the incredible skyline and is perfect for a sundowner. Especially on weekends, there can be a long queue waiting for the elevator to take you up and it’s a place to see and to be seen.

In its neighborhood you’ll find the RAISED | An Urban Rooftop Bar, another great bar. Although it is not as high as the London House one, I can totally recommend it. They have cozy seating options and offer an excellent view over the skyline on the other side of the river. Located next to the Millennium Park is Cindy’s. It’s a restaurant and rooftop bar with a perfect view over the Cloud Gate and the park.

For bar hoppers, you’ll find great options along the Chicago Riverwalk. Little bars and wineries pop up around every corner and offer relaxed seating right next to the river. Locals also go there for some afterwork activities, so be ready for a relaxed and mixed crowd of business people, locals, and you. There are also little bars located in the West Loop and around West Randolph Street. If you’ll pick a restaurant for dinner there, you can immediately switch to nightlife afterwards.

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For cultural explorers.

A must for all cultural explorers is a visit at the theater. To experience one of the finest arts and be surrounded by historical architecture, Chicago weekend getaway has it all in Chicago’s Theatre District. In the central city, you’ll find different theaters hosting beautiful stage plays, broadway musicals, and shows. Just to name a few, the famous one (and picturesque too) is the Chicago Theatre. It was founded in 1921 and originally opened its doors as a cinema. Besides their breathtaking plays nowadays, they offer behind-the-scenes historical tours for visitors. To check on their current shows and grab your tickets, go here.

I once went to the Cadillac Palace Theatre and had an amazing evening at this broadway theatre inspired by Versailles. Snuggling into the comfy red seats while slipping on a glass of champagne and watching a brilliant show, wow. For Cadillac Palace Theatre, get your tickets here. Another great theatre is the Goodman Theatre, the oldest non-profit theatre in Chicago. Tickets are available here. Are you ready to explore more in the Theatre District? Check out a full guide to Chicago theaters including independent theaters and so much more.

Another great recommendation is the Jay Pritzker Pavilion in Millennium Park. They frequently play concerts in summer during their ‘The Millennium Park Summer Music Series’ that are totally free! On stage they’ll welcome national and international musicians and artists. Seating is based on a first-come-first-served basis for these events on weekdays from typically June to August. This is for further information.

A great pick for art lovers, is the Art Institute of Chicago. It is an incredible art museum founded in 1866 and hosts more than 300,000 pieces of art. Visit art by Vincent van Gogh or Claude Monet, and of course American art. Check out further information about the institute.

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For sight hoppers.

The main sight of Chicago is its architectural richness and the spectacular skyline. If it’s the famous The Wrigley Building with its iconic tower clock, or the Willis Tower and so much more beautiful buildings. First, you can explore them by foot and a great walk along the Chicago Riverwalk. Second, you could board a boat on the river. At Riverwalk Ferry Terminal you’ll find little kiosks selling tickets and the departure and arrival terminal of the boats. Hopping on a boat is perfect for you, when you need a little guidance to the architectural paradise. The boat will take you up and down the river, give insights on historical sights, architectural wonders, and the development of Chicago.

Further down the river, you’ll find the harbor and the Navy Pier. In this area you’ll find a lot of things to spend a good time. If it’s a museum, the Chicago Shakespeare Theater, shops, restaurants, or the Ferris wheel that offers and amazing view over Lake Michigan and of course Chicago.

Another breathtaking panoramic view over Chicago offers a platform at John Hancock Center near the Magnificent Mile. From the ‘360 Chicago Observation Deck’ on the 94th floor you’ll definitely don’t miss a thing on Chicago’s streets or beach or harbor. Better buy tickets in advance to beat the tourist crowds. Totally recommended is the visit during sunset. They offer really cool events there, too: yoga classes named ‘360 Sky Yoga‘, a ‘360 Hoppy Hour‘ at the bar, or ‘360 Sky Art‘ courses from 1,000 feet above the ground that will take your breath away. Regarding your perfect weekend getaway to Chicago city, make sure to book your tickets in advance to not miss an event.

Definitely recommended is a walk through the Millennium Park and a visit of the famous Cloud Gate. The surface of the silver bean sculpture perfectly reflects its surroundings such as Chicago’s skyline and you, when you’re taking a picture. It’s an amazing spot to take instagramable pictures there. Further down south and a stroll along the lakefront starts Grant Park. It has iconic Buckingham Fountain, a rose garden, and many more green stops to get perfectly lost and relaxed.

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For chilli vanillis.

After non-stop sightseeing, you might want to relax a bit. As already mentioned, the many greeneries and parks in Chicago are perfect. You can walk, take a seat, and enjoy. The best ones are at the lakefront from North to South: There is Lincoln Park, Millennium Park, and Grant Park – just to name a few. In winter, this is also worth to visit, when the greeneries get covered under a huge white blanket.

Time to relax is also given at Chicago Riverwalk. Right next to the river, you’ll find great spots to sit down and relax by the water. At the many kiosks along the walk, you can grab something to eat and drink and continue enjoying the river view during your weekend getaway to Chicago.

And of course, don’t miss the many beaches to enjoy in summer. The closest to the city center is Oak Street Beach. Bright white sand and large sandy shores offer a relaxing summer hotspot to everybody. Turning around on your beach towel offers breathtaking view over Chicago skyline. Beach facilities are available on-site. Next to Lincoln Park, there is North Avenue Beach offering a lot more options to spend a day on the beach. If you want to enrich your relaxing day during your weekend getaway with some beach activities in Chicago, check out chapter one above.

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For fashionistas.

Of course, the weekend getaway to Chicago can convince you with many shopping options. You’ll love it girl! You can find huge shopping malls in central Chicago. For example, Water Tower Place, The Shops at North Bridge, and 900 North Michigan Building. Other most great shopping spots are located along Magnificent Mile. Bloomingdale’s and Macy’s is also available at several locations in Chicago. Check out more spots to go shopping, whether it’s for luxury products or unique vintage pieces.

There are also street markets open to public and farmers markets to shop incredibly fresh and local products. City Market at Daley Plaza is open every Thursday from May to October. Green City Farmers Market is open year-round on Wednesdays and Saturdays and located in Lincoln Park. In winter it moves to an indoor location. This is for further information on the markets in Chicago.

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Ready girl to explore New York City? I am sure you are – get my best tips for your next solo trip to this incredible American city here.

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// Disclaimer //  I was not paid for my reviews and recommendations mentioned in this blog post. The views and opinions expressed in this blog post are purely my own and can be considered as honest evaluations.

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Have something to add or want to share your experiences? Please leave your comments and thoughts below and share these insights with other travel lovelies. Chicago already awaits you

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