Weekend Getaway: Chicago
Get to know the heart of the Midwest with a trip to the iconic Windy City. This 3-day itinerary offers a blend of iconic attractions, urban sophistication, and cultural treasures to immerse yourself in the vibrant energy of the city.
Getting There
Driving - like any Midwestern city, you can of course drive to Chicago. Watch out for steep parking prices and congested traffic for much of the day. If you are reliant on a car, check for hotels that include parking on-site or that has garage access nearby.
Train - Chicago also has a bustling Amtrak station, with direct routes coming from many of the major cities throughout the Midwest.
Park and Ride - Chicago is an incredibly commuter friendly city, with numerous Park and Ride stations located along the lakeshore of Lake Michigan. If you’re coming from the East (Indiana, Michigan, Ohio), you can park at many of the stations for free and catch the train into downtown via the South Shore Line for a fare of around $10 per person. The route has trains leaving every half hour to an hour during the week, and every hour on the weekend. Click here for an updated timetable on the South Shore line. From the Millenium Park station, it is only a short walk to the River North neighborhood and the Freehand Chicago hostel described below.
Before we get started, check out these top experiences in Chicago to elevate your trip!
Day 1
Escape the hustle of the city and enjoy the Lincoln Park Zoo & Conservatory, an urban oasis that will immerse you in a blend of wildlife, greenery, and education. Encounter a diverse range of animals at the zoo, from exotic species to familiar favorites. The well-designed exhibits provide an up-close view of creatures in habitats that mimic their natural environments. The zoo is open daily from 10:00 am and admission is always free!
After spending some time at the zoo, make your way to the nearby Lincoln Park Conservatory. The park is the largest in the city and is run entirely by volunteers. The historic greenhouse complex is home to a diverse collection of plants from around the world. As you stroll through its various rooms, you’ll encounter tropical plants, palms, ferns, and vibrant flowers. Visit one of their seasonal events, such as the Sweet Gnome Chicago Flower Show, running from February to May 2024. The conservatory is open Wednesday - Sunday, 10:00 am to 5:00 pm. Visits are free, but a timed entry reservation must be made in order to enjoy the experience.
Nearby the conservancy, you’ll find a number of dining options to stop for lunch that will suit different preferences. Some popular choices include North Pond, a fine dining restaurant with a seasonal menu and picturesque view overlooking Lincoln Park, and Cafe Brauer, located in the historic building near the zoo and providing a charming setting with views of both the pond and the skyline. After lunch, head back to downtown to continue exploring the Magnificent Mile and Wrigleyville.
Coffee lover? Cocktail connoisseur? The Starbucks Reserve Roastery is the perfect next stop for you. With five floors to explore, the largest Starbucks in the world is a sight to behold. Enjoy an espresso martini flight or one of their smoky bourbon options while overlooking the Magnificent Mile below. If visiting during the summer months, check out the rooftop terrace for breathtaking skyline views in a serene, elevated atmosphere. Beyond sampling the drinks the roastery has to offer, you can engage in coffee seminars, attend brewing classes, or simply watch as baristas expertly pour over your coffee. It’s an opportunity to deepen your appreciation for the craft. Even if you’re not a coffee drinker, the roastery is not just a a coffee haven, but also an artistic masterpiece. Intricate murals, handcrafted mosaics, and custom-made furnishings contribute to the unique ambiance, creating an environment where every detail tells a story of craftsmanship and passion.
In the evening, take the train to Wrigleyville to catch a Cubs game at the historic Wrigley Field. One of the oldest parks in Major League Baseball, Wrigley will celebrate it’s 100-year anniversary in 2024. Grab a hotdog and peanuts and enjoy the game. Consider yourself lucky if you get to witness the iconic rivalry between the northside Cubs and southside White Sox.
Day 2
Start your morning with a stop at one of Chicago’s many cafes for a coffee and a pastry. We loved Firecakes’ wide selection of small-batch artisan donuts, with flavors like pistachio, orange poppyseed, and wildflower honey. Firecakes has numerous locations around the city, click here to find the one nearest your hotel.
After enjoying your light breakfast, make your way to the museum campus to explore the Field Museum, where you will find extensive natural history exhibits, and the Shedd Aquarium, to encounter marine life from across the globe. For non-residents and tourists, admission to Shedd Aquarium is $40, while the Field Museum is $27. If you plan to visit multiple museums during your trip to Chicago, I recommend purchasing the Chicago CityPASS. For $134 per person, you will receive admission to the aquarium as well as Skydeck Chicago, and also the option to choose 3 of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, Adler Planetarium, and Shoreline Sightseeing Architecture River Tour.
Once you have explored the museum campus to your liking, enjoy lunch at one of the many nearby food trucks (bonus points if you go for a Chicago dog) and walk through Grant Park, also known as Chicago’s Front Yard. The park covers over 300 acres and is filled with a blend of green spaces, iconic landmarks, and recreational facilities. In the center of the park is Buckingham Fountain, one of the largest in the world, offering stunning water displays and periodic light shows. Adjacent to the park is the Art Institute of Chicago, and is a world-class art museum definitely worth exploring.
Make a visit to the famous Navy Pier. Ride the Ferris wheel, dine at one of the restaurants along the water, and enjoy the stunning views of Lake Michigan and Chicago skyline. Explore Pier Park for amusements, enjoy boat tours, catch a performance at the iconic Chicago Shakespeare Theater, and wander through the shops for the perfect souvenir. If you are visiting with kids, the Chicago Children’s Museum on Navy pier provides interactive exhibits and educational activities. Depending on the time of year, Navy Pier hosts fireworks displays, providing a spectacular nighttime show over stunning Lake Michigan. Check out their calendar to see if it coincides with your trip.
Cap off your evening by catching a Broadway show at one of the several theaters across the city. On our most recent visit in November 2023, we finally got to see Hamilton at the James M. Nederlander theater. We ended up buying tickets the day of and sat in the front row for a fraction of the original cost. It was such an unforgettable experience!
Day 3
Begin your last morning in the city with brunch at Wildberry Pancakes & Cafe. There are locations near Millennium Park and the Water Tower Place. It is some of the best breakfast food I have ever had, and because of that, the wait tends to be pretty long. While you wait, walk across the street and through Millennium Park to see the Bean. One of Chicago’s most noteworthy landmarks is Cloud Gate, affectionately referred to as “the Bean”. The sculpture created by artist Anish Kapoor was unveiled in 2006, and the name comes from its kidney bean-like shape. Its seamless, mirror-like surface distorts and reflects the cityscape, creating a surreal and captivating visual effect. The underside of the sculpture allows visitors to walk beneath it, providing unique perspectives and photo opportunities.
Conclude your weekend in Chicago with an architecture riverboat tour in the Chicago River. If you have opted for the Chicago CityPASS, this is included as one of your choices. Chicago is renowned for its architecture and is often considered the birthplace of the skyscraper. The Home Insurance building was completed in 1883 and is considered the world;s first skyscraper with a steel frame. Chicago’s architecture is diverse, featuring a mix of historic and modern styles. Notable architects like Frank Lloyd Wright and Mies van der Rohe have left their mark on the impressive city scape. Say goodbye to the city with this boat tour along the Chicago River to see some of the most popular sights.
After your tour, it is time to begin your journey back home, whether that is with a flight from O’Hare International Airport or with one of the options discussed above. As you bid farewell to the Windy City, you will be dreaming about returning for another enchanting trip in the future. Keep reading for the best accommodation and dining options the city has to offer.
Where to Stay
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Located in the River North neighborhood, this hostel is the perfect option for travelers looking for accommodation close to all of the city’s main attractions. The property is also home to Broken Shaker, award-winning cocktail bar in the lobby. Rooms range from king and queen private options, as well as 4-bed mixed dorms. We stayed in a dorm on our last visit and enjoyed getting to know and sharing stories with our roommates.
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Nestled among the Art Deco masterpieces and modern skyscrapers that make up the beautiful skyline, you will find the perfect boutique hotel when you choose the Virgin Hotel Chicago. Whether you choose a traditional chamber or a suite, keep your stay in Chicago comfortable with adjustable spaces for living, dressing, and sleeping. The Virgin Hotel in Chicago boasts three diverse restaurants and cocktail bars perfect for relaxing after a long day of exploring the city. Traveling with your pet? An added bonus is pets staying in pet-friendly rooms, with no additional fees and no breed or size restrictions.
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The Drake Hotel Chicago is located near the popular landmarks in the city like Navy Pier and the Water Tower Place, making it the perfect home base for a weekend spent in the city. You will experience true luxury with beautiful suite options and luxurious dining rooms. Take part in a classic afternoon tea in Palm Court, which was once visited by Queen Elizabeth II and Princess Diana. The hotel is also home to Coq D’oR, one of the first venues to secure a post-Prohibition liquor license, and today serves a variety of cocktails and comfort foods. Room service is available for each of the property’s restaurants.
Where to Eat
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Located in Chicago’s West Loop, you will find this acclaimed restaurant helmed by chef Stephanie Izard. Known for its inventive and bold approach to flavors, the restaurant offers a contemporary American menu with a focus on small plates meant for sharing. The interior is bright and energetic, featuring a mix of rustic and modern elements. The open kitchen adds to the dynamic atmosphere, allowing diners to catch a glimpse of the culinary creativity happening behind the scenes. Signature items on the menu include the Hamachi Poke, Crispy Pork Belly, and Goat Empanadas. Enjoy a Sticky Toffee Pumpkin Spice Cake or Coconut Creme Caramel for dessert. Girl & the Goat has a well-earned reputation as one of Chicago’s premier dining destinations, making it a must-visit while in the city.
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Chicago is renowned for its distinctive deep-dish pizza style and its signature caramelized crust. With locations around the city, Pequod’s is the pizza of choice for Chicago locals. The highlight of Pequod’s pizza is the pan-style crust, caramelized around the edges and creating a unique and flavorful bite. Choose from a variety of options, including classic combinations and inventive choice. Each ingredient is thoughtfully layered, resulting in a satisfying and indulgent pizza experience every time.
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Step inside and be instantly transported to the breezy, coastal vibes of California right in the Windy City. With its beach-house-inspired decor and light-filled ambiance, this eatery offers a refreshing escape from the urban bustle. The menu reflects its California inspiration, featuring fresh and seasonal ingredients. From colorful salads to freshly baked pastries, the cuisine embraces a light and wholesome approach. Enjoy this taste of the West Coast right in the heart of Chicago.
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This is a must-stop brunch place for any trip to Chicago, with locations in Millennium Park and the Water Tower Place. Wildberry offers delectable pancakes and extensive breakfast menu offering a fusion of classic and innovative flavors. The wild berry pancakes, a signature dish, are a huge plate of fluffy pancakes adorned with a medley of fresh berries. The presentation is as vibrant as the flavors, making it a feast for both the eyes and the palate. Beyond pancakes, the cafe boasts an array of breakfast options, from omelets and crepes to biscuits and gravy and decadent french toast.
Have an extra day or two in the city and looking to fill your time? Here are a few bonus ideas we found that you will LOVE:
WNDR Museum Chicago
Price: $32 per person
Hours: 12pm-8pm Monday-Thursday, 10am-8pm Friday-Sunday
“WNDR Museum is an interactive experience: a multi-sensory showcase of art and technology. [Their] message is simple: We are all artists. And as artists, [their] visitors are more than passive onlookers. Whatever they do in the museum, IS art.”
The experience took us about an hour and 15 minutes to walk through, including stops to take pictures and enjoy the art. One of our favorite exhibits was The Wisdom Project, which allowed visitors to share something they know for sure, and post it to the wall. We spent a few moments reading through the advice, heartfelt love, and encouragement people were sharing with the world, and walked away feeling very optimistic and hopeful.
Visiting during the winter? Check out WNDR’s ‘Winter WNDRland’ event running from November 24th - January 15th, transforming some of the museum’s most loved exhibits into a snowy frozen landscape. The Iced Inn, pop-up bar, will be available serving warm drinks including mulled wine and hot whiskey cider, as well as non-alcoholic options. The WNDR ski pass, given at the entrance, can be redeemed for complimentary s’mores.
The Barrel Run
Price: $85 per person
Hours: tours offered at 11am and 3:30pm, most Fridays and Saturdays
Interested in a unique way of seeing the city and trying some local brews? Look no further than The Barrel Run, a craft brewery tour aboard The Barrel Bus, an old bus that has been converted into the shape and rustic style of a whiskey barrel.
We did the tour back in November 2023 and had a wonderful time. It was a great way to experience different parts of Chicago without having to walk a ton outside in the cold. We also really enjoyed our tour guide, who told stories and gave context for Chicago during the prohibition days and the history of bootlegging. We stopped at three different breweries on our tour, but were told that the order/number of stops depends on the day and traffic. Each of the stops were unique, and places we would not have found on our own. Click here to see a list of our favorite breweries we checked out in Chicago. The tour includes roughly 50 oz. of beer, and there is time allotted for participants to order additional drinks if they wish.
The only downside I saw to this tour was that drinks were pre-selected; we did not get to choose which beers came in the included sample, which meant drinking mostly pale ales and pilsners. If that is your preferred style of beer, then this will not be an issue. But if you are like us and want to try several different types, it is good to know in advance what to expect. Overall, the Barrel Run was a really fun way to spend a few hours during our weekend trip to Chicago and I highly recommend it. Clickhere to book your tour now.