Chicago Weekend: Where to Stay, What to See With CityPASS

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The Cloud Gate mirrored sculpture in Millennium Park is worth a stop, reflecting Chicago’s skyline and visitors in its stainless steel surface.
A visit to the free and iconic Cloud Gate (AKA the bean) mirrored sculpture in Millennium Park is a must. Photo credit: Emily Molina

I’ve traveled to enough sports tournaments with my daughter to know how to turn competition weekends into mini-getaways. This spring, we traveled to Chicago for a major volleyball tournament. One stellar hotel, and two CityPASSes later, here’s how to make the most of your time between matches, balancing volleyball, sightseeing and a fun girls’ weekend.

Game Plan for Your Weekend

  • How to fit sightseeing into tight tournament schedules without adding stress.
  • My honest take on using CityPASS in Chicago: what’s worth it and how we made the best of it between games.
  • Easy and inexpensive ways to get around the city without wasting time.
  • Try Chicago’s iconic food classics between matches, so even meals feel like part of the adventure.
  • Why staying at the Palmer House Hilton helped simplify logistics and maximize our limited downtime.

        Editor’s note: The writer was hosted.

        Fitting In the Fun

        Banners hang high above the concourse at McCormick Place Conference Center during the Chicago Windy City National Qualifier.
        Banners at McCormick Place Conference Center during the Chicago Windy City National Qualifier. Photo credit: Emily Molina

        Seasoned sports parents know that getting AM or PM assigned play time matters. Called a “wave” in sports parlance, the game assignment time shapes everything else. Trust me, you want an AM wave, but that doesn’t always happen.

        • AM wave: Early wake-up (think crack-of-dawn), but you’re done in time to enjoy the rest of the day.
        • PM wave: Slower start, but you’ll likely leave the venue late, have less daylight and less time for exploring during business hours.

        That said, you can make either schedule work. After all, you didn’t travel all this way just to sit in a convention center. We always find a way to build in something fun.

        With a PM wave, treat your morning like your sightseeing window.

        • Plan something low-stress and close to your hotel or tournament venue.
        • Keep your timing flexible so you’re not rushing straight from an activity to warm-ups.
        • Build in time for meals so no one is scrambling or running on empty.
        • Wrap up early enough to allow for travel time, parking and room for switching into game mode.

        Even with a later start, there’s plenty of time to explore; you just have to be more intentional about it.

        If you’re on an AM wave, you’re in a great position to stack your afternoon and evening with activities once games wrap up.

        SheBuysTravel Tip: Try to end your outing about 60–90 minutes before you need to be at the sports venue. It gives you a cushion and keeps the day from feeling rushed if any last-minute things come up.

        Are you ready to explore off the beaten path? Let us inspire you!

        My daughter and her team competing in a volleyball tournament at McCormick Place on the court inside a large convention hall.
        High-energy tournament action as the team competes at McCormick Place in Chicago. The atmosphere is loud, intense, and exhausting, making downtime and fun activities in the city just as important as the games themselves. Photo credit: Emily Molina

        Making the Most of Chicago CityPASS on a Tight Schedule

        Skydeck Chicago just before sunset, with warm light over the city skyline.
        Skydeck Chicago was one of two included CityPASS attractions, plus we got to choose 3 more. Photo credit: Emily Molina

        CityPASS is one of the easiest ways to save both time and money while exploring Chicago. After already spending a small fortune on club volleyball, travel and accommodations, it was a welcome bonus.

        Our pass included immediate access to must-see attractions like the Shedd Aquarium and Skydeck Chicago. From there, we were able to choose three additional attractions from the list below.

        Many offer flexible scheduling throughout the day, making them easy to fit in either after an AM wave wraps up or before a PM wave begins:

        Our first pick was Skydeck Chicago, and it’s hard to top, especially if you time your visit right before sunset. You can feel the movement as the elevator zooms up the 103 floors of Willis Tower. Your ears pop, and the excitement builds before you even get there.

        We were lucky to catch an AM wave for the volleyball tournament that day, which gave us enough time to get there for crystal-clear views of the city, as the sun set, a popular time, and that warm golden light that made great photos of an unforgettable skyline.

        Chicago skyline viewed from the Skydeck Chicago at Willis Tower with the city stretching into the distance.
        Chicago begins to glow as the city lights twinkle below Skydeck Chicago at Willis Tower, definitely worth the trip. Photo credit: Emily Molina

        Next, we reserved space on a Shoreline Sightseeing Architecture River Tour.

        The 90-minute, moderated tour is an activity that works for both AM and PM waves, with tours available just about all day. It’s a smooth and scenic boat ride. You feel the wind on your face. Learning about the city’s architecture along the way makes it even more engaging.

        Seeing so many historic landmarks standing alongside newer, modern ones, each reflecting a different era of Chicago’s ever-evolving skyline, and the architects who helped shape it, was very inspiring.

        Watching the city continue to grow with each new addition felt especially meaningful, knowing my daughter hopes to one day become an architect herself.

        Chicago skyline viewed from the upper deck of Shoreline Sightseeing Architecture River Tour.
        A Shoreline Sightseeing Architecture River Tour is a great CityPASS pick, offering a unique way to experience Chicago from the water while learning about its iconic skyline. Photo credit: Emily Molina

        SheBuysTravel Tip: For the Shoreline Sightseeing Architecture River Tour, sit on the outer edge of the boat for unobstructed skyline photos and better views of the river-level details. Make reservations in advance for a specific time slot.

        We visited the Art Institute of Chicago on an afternoon near closing, and it wasn’t busy at all. We were thoroughly impressed by the number of galleries. We especially enjoyed the Impressionist collection and works by Renoir, Manet and others.

        Post-Impressionist classics by masters like Van Gogh made the visit even more memorable, especially seeing such iconic paintings up close and in person.

        Vincent van Goghs self-portrait on display at the Art Institute of Chicago with him in a blue jacket against a swirling blue-green background.
        Seeing Van Gogh’s self-portrait in person at the Art Institute of Chicago is unforgettable. The texture, color and emotion feel completely different up close. One of those artworks that makes the whole museum visit worth it. Photo credit: Emily Molina

        We also visited the ongoing installation A New View: 20th- and 21st-Century Architecture and Design, which offers an inspiring look at visionary city plans, furniture and experimental design.

        My daughter looking at a modular cube installation in A New View: 20th- and 21st-Century Architecture and Design at the Art Institute of Chicago.
        My daughter exploring the modular cube installation in A New View: 20th- and 21st-Century Architecture and Design at the Art Institute of Chicago. Photo credit: Emily Molina

        Yes, we already went to one, but you can never have too many observation decks. Each offers a different perspective of the city. 360 CHICAGO Observation Deck was high on our list because of CloudBar, which we really wanted to experience.

        Located on the 94th floor alongside the main viewing area, CloudBar is included with general admission and open to all ages during the day. Alcoholic beverages are available only to guests 21 or older with a valid ID.

        SheBuysTravel Tip: CloudBar is family-friendly during the day, but if you’re traveling with kids, plan earlier hours since evening crowds tend to be more adult-focused.

        Interior view of CloudBar at the 360 CHICAGO Observation Deck on the 94th floor, with floor-to-ceiling windows overlooking sweeping panoramic views of the Chicago skyline and Lake Michigan.
        CloudBar at the 360 CHICAGO Observation Deck on the 94th floor offers panoramic views of the Chicago skyline and Lake Michigan, a perfect stop included with CityPASS for unforgettable city views from above. Photo credit: Emily Molina

        Easy Ways to Get Around Chicago Without Wasting Time

        CTA ‘L’ train arrives just under McCormick Place through downtown Chicago, as we prepare to ride back to the hotel.
        CTA ‘L’ train arrives just under McCormick Place in downtown Chicago as we prepare to ride back to the hotel after the tournament. Photo credit: Emily Molina

        The Chicago Transit Authority (CTA) makes it easy to get around, whether you’re riding the bus or taking the train on the Chicago ‘L’.

        We used a variety of transportation options to get where we needed to go, including rideshare between downtown and the airport, as well as CTA buses and the ‘L’ to reach the tournament venue.

        It is also possible to take the train from the airport to downtown, depending on your preference (and amount of luggage).

        The CTA bus arrives at our stop on its route from the hotel to the tournament venue.
        The CTA bus arrives at our stop on its route from the hotel to the tournament venue, offering a simple, affordable, and easy way to get around the city. Photo credit: Emily Molina

        Getting to the tournament on time is always a priority, since you have a set arrival schedule and can’t afford delays. We took the bus to the venue because it was the least expensive option, with a stop just around the corner from our hotel and a straightforward 15– to 20-minute ride. It was a comfortable, clean ride where we could sit back and look out the window.

        Crowded CTA ‘L’ train platform in Chicago after games finish, with groups of people waiting together as everyone departs at the same time following the event.
        Crowded CTA ‘L’ train platform after games end in Chicago, with an exciting rush of energy as everyone heads home at the same time. Photo credit: Emily Molina

        Once you’re all done competing for the day, the return trip is more relaxed and faster on the CTA train, which runs under McCormick Place.

        The platform can get crowded as everyone heads out at the same time after events end. It was kind of fun being part of the rush and energy of the packed train. Most importantly, we found the system easy to navigate, clean and safe throughout our stay.

        Overall, we had the most fun just walking through the city’s streets whenever we could, like to the Navy Pier, or along the Chicago Riverfront, popping into little shops, grabbing a coffee and taking in the sights and energy of Chicago life along the way.

        View of the iconic Ferris wheel at Navy Pier, rising above the waterfront with Lake Michigan.
        The Ferris wheel at Navy Pier, such a fun place to walk around, take in the views, and enjoy the energy along the waterfront. Photo credit: Emily Molina

        Chicago’s Iconic Food Classics Are All Part of the Adventure

        Classic Chicago deep dish pizza at Giordano's, showing a thick, cheesy slice with rich tomato sauce and golden crust on a plate, highlighting the iconic style of Chicago pizza.
        Enjoying a classic Chicago deep dish pizza at Giordano’s. Photo credit: Emily Molina

        Trying some of Chicago’s classic foods is part of the fun and adventure, adding another layer to our time in the city. While we managed Chicago deep-dish pizza on two occasions, we somehow missed a classic Chicago-style hot dog.

        During the tournament, we tried to stay balanced with healthier meals and snacks, and to stay hydrated to keep up with the busy days.

        Giordano’s was the place for deep-dish pizza with rich, cheesy layers, buttery crust and hearty tomato sauce-the city is known for. That first memorable stringy, cheesy, happy bite brought all smiles and laughter around the table. With multiple locations across Chicago, it’s an easy way to enjoy a true local favorite no matter where you are in the city.

        “Eat Pizza” sign displayed inside Giordano's, capturing the casual and inviting atmosphere of the iconic Chicago deep dish pizza restaurant.
        The sign said “Eat Pizza,” so naturally we did, digging into a classic Chicago deep dish at Giordano’s. Photo credit: Emily Molina

        We were surprised to find so many açaí bowl spots in the downtown area, great news when you’d rather skip the long convention center lines for this popular (and often overpriced) favorite among the volleyball crowd.

        Picking one up ahead of time, this part-healthy-part indulgent treat, was easy with places like Deep Purpl Açaí Bowls just around the corner from our hotel.

        Interior of Deep Purpl Acai Bowls near our hotel in downtown Chicago, showing the bright and casual café space that quickly became one of our go-to stops during the trip.
        Inside Deep Purpl Açaí Bowls, a bright and casual downtown Chicago spot near our hotel that quickly became our go-to for the popular, tasty treat. Photo credit: Emily Molina

        Most importantly, there was never a shortage of nearby coffee shops either, an essential during tournament time, when a steady supply of caffeine keeps parents powered through long, early or late, very full days.

        One such find that quickly became a favorite is Goddess and the Baker. Hunting down a coffee shop before an early match one morning, the aroma of coffee mingling with the city’s morning energy pulled me in. I returned on more than one occasion.

        Bakery case inside Goddess and the Baker, displayed in the most adorable and fun café setting, filled with fresh pastries and colorful baked treats.
        Bakery case inside Goddess and the Baker, set in the most adorable and fun café atmosphere, which quickly became our morning go-to for coffee and pastries. Photo credit: Emily Molina

        Brunch at the delightfully colorful Sugary Chicago, conveniently located on Michigan Avenue’s Magnificent Mile, was a special treat we saved towards the end of the tournament. An over-the-top spread of waffles, crepes, pancakes, fresh fruit, yogurt, pastries, milkshakes, ice cream, tea and coffee, all beautifully piled high in a playful brunch experience.

        Colorful umbrellas and storefront of Sugary Chicago on Michigan Avenue’s Magnificent Mile, where we enjoyed a celebratory brunch that felt like the perfect end-of-tournament reward.
        Sugary Chicago on Michigan Avenue’s Magnificent Mile, where we enjoyed a celebratory brunch that felt like the perfect end-of-tournament reward. Photo credit: Emily Molina

        Why the Palmer House Hilton Was the Perfect Home Base for Our Stay

        Exterior view of the historic Palmer House Hilton, a restored downtown Chicago hotel with classic architecture and a central location.
        The historic Palmer House Hilton was the perfect home base for our trip, with easy access to public transit and many of Chicago’s top attractions. Photo credit: Emily Molina

        The historic Palmer House Hilton was the perfect home base for our trip, centrally located with easy access to the convention center, restaurants, public transit and many of Chicago’s top attractions. After long volleyball days, it made getting around the city simple while still giving us a chance to experience a classic piece of Chicago history.

        The stunning lobby of the Palmer House Hilton featuring elegant historic architecture, lively lobby bar, chandeliers, and ceiling fresco.
        We loved relaxing in the breathtaking lobby of the Palmer House Hilton, constantly staring up at the incredible ceiling fresco by Louis Pierre Rigal, later restored by Lido Lippi, who also worked on the Sistine Chapel. Photo credit: Emily Molina

        Why We Loved Staying at the Palmer House Hilton

        • Stunning historic lobby featuring the breathtaking ceiling fresco painted by French artist Louis Pierre Rigal.
        • Delicious dining at Lockwood Restaurant and cocktails at the Lockwood Lobby Bar.
        • The famous Palmer House Brownie: rich, fudge-like chocolate topped with a decadent walnut-and-apricot glaze.
        • Convenient grab-and-go options at Lockwood Express.
        • Express-2-You room service delivery or easy pickup from Lockwood Express.
        • Potter’s: the hotel’s speakeasy-style cocktail bar.
        • On-site Starbucks for quick coffee runs between matches.
        • The hotel has its own history museum and guided history tour.
        • One of the nicest indoor pools we’ve ever experienced.
        • Comfortable lounge and sitting areas throughout the property.
        • The Palmer House Health Club fitness center.
        • The incredible Spa at Palmer House is perfect for relaxing after long tournament days.

        Dining at the Palmer House Hilton

        Interior view of the Lockwood Lobby Bar at the Palmer House Hilton, featuring an elegant, historic setting with warm lighting, classic architectural details.
        The Lockwood Lobby Bar at the Palmer House Hilton, an elegant, historic spot for a drink, a bite, and timeless Chicago atmosphere. Not nearly enough time here. Photo credit: Emily Molina

        One thing, among many, that we loved about our stay was the dining experience, especially breakfast each morning at Lockwood Restaurant. Starting the day there with a hearty breakfast quickly became one of our favorite parts of the trip and helped us prepare for the long days. In the evenings, nothing could compare to dining in the lobby, next to the bar beneath the beautiful ceiling, which we couldn’t stop looking up at. It was the perfect place to relax after a busy day, whether enjoying dinner, drinks or just soaking in the ambiance.

        Another perk was Lockwood Express for quick grab-and-go meals between activities, as well as the Express-2-You room service and pickup options.

        The Famous Palmer House Brownie

        Close-up of the famous Palmer House brownie at the Palmer House Hilton, a rich, fudgy chocolate dessert topped with a glossy walnut and apricot glaze, known as a Chicago classic.
        Close-up of the famous Palmer House brownie at the Palmer House Hilton, a rich, fudgy chocolate dessert topped with a glossy walnut and apricot glaze. Honestly, we could have eaten this morning, noon, and night, it was that good. Photo credit: Emily Molina

        It was in the hotel lobby one evening that we had our first taste of the famous Palmer House brownie, rich, fudgy and known for its dense texture, deep chocolate flavor, and decadent walnut-and-apricot glaze. Created in 1893 for guests attending the World’s Columbian Exposition, the brownie was specially designed as an easy-to-carry treat for boxed lunches and would become something of an icon for the hotel, and still is today.

        Bars

        Exterior view of Potter’s, the speakeasy-style bar at the Palmer House Hilton, featuring a discreet, classic entrance that hints at its intimate, hidden cocktail lounge atmosphere in downtown Chicago.
        Exterior of Potter’s, the speakeasy-style bar at the Palmer House Hilton, a hidden gem I didn’t get a chance to visit this time. Photo credit: Emily Molina

        Although sadly, I didn’t get the chance to experience it for myself, Potter’s Bar sounded like it was just up my alley. Inspired by Chicago’s Prohibition-era speakeasies, what’s not to love about a sophisticated, vintage atmosphere that nods to the city’s notorious past? Maybe next time.

        History & Experience

        The hotel’s grand lobby is truly one of a kind, a breathtaking space that feels almost Sistine Chapel-like in its scale and beauty. The iconic ceiling fresco painted by Louis Pierre Rigal gives the space a larger-than-life presence. In fact, it underwent a major restoration in 1996, led by renowned Italian artisan Lido Lippi, who also worked on the restoration of the Vatican’s Sistine Chapel.

        View through a window into the history museum at the Palmer House Hilton, showing curated exhibits that highlight the hotel’s rich heritage and long-standing place in Chicago history.
        View through the window of the history museum at the Palmer House Hilton, showcasing its curated exhibits on the hotel’s rich past and Chicago’s history. I was disappointed I didn’t get a chance to visit here. Photo credit: Emily Molina

        There is also an on-site history museum filled with fascinating artifacts, vintage photographs and memorabilia that help bring the hotel’s remarkable story to life. Guided history tours offer guests the chance to learn about the legendary romance of Potter and Bertha Palmer, the hotel’s survival after the Great Chicago Fire and its lasting place in Chicago history.

        Amenities & Relaxation

        Person relaxing in the indoor pool at the Palmer House Hilton, featuring a calm, inviting swimming area with warm lighting and a comfortable, resort-like atmosphere.
        Me relaxing in the indoor pool at the Palmer House Hilton, easily one of the nicest hotel pools I’ve ever experienced. Photo credit: Emily Molina

        From one of the most impressive hotel pools we’ve ever experienced to an exceptionally nice and well-equipped fitness center, the wellness amenities at the Palmer House really stood out to us. After long days, it was so nice to come back and unwind with a relaxing dip in the pool whenever we had the chance. While my daughter was getting more than enough cardio from volleyball, I appreciated having such a great fitness center available to squeeze in a workout whenever I wasn’t busy leading the cheering section from the sidelines.

        Interior of the fitness center at the Palmer House Hilton, featuring modern exercise equipment, clean design, and a well-equipped space for guests to work out during their stay.
        The fitness center at the Palmer House Hilton-we were blown away by how much equipment it had; such a well-designed, impressive gym. Photo credit: Emily Molina

        The Spa at Palmer House

        Entrance to the spa at the Palmer House Hilton, featuring a calm, inviting entryway that sets a relaxing tone for wellness and treatments.
        Entrance to the spa at the Palmer House Hilton, exactly what we needed and couldn’t wait for after long, busy days. Photo credit: Emily Molina

        This was easily the best treat of all, and definitely the one we needed most after long tournament days filled with nonstop whistles, crowds, and noise. Saving the Spa at Palmer House experience for the end of our trip turned out to be the perfect decision, giving us a chance to finally slow down, recharge and enjoy some much-needed peace and relaxation. From the spa’s extensive menu of services, we chose signature facials, which felt incredibly refreshing after days of being constantly on the go.

        After changing into robes and slippers in the private changing rooms, we relaxed in the spa’s cozy sitting areas with teas and refreshments while we waited for our appointments. It was everything we could have imagined: warm towels, calming products and gentle facial massages.

        Afterward, the luxurious shower suites and thoughtfully stocked products made it easy to get ready for our final evening in the Windy City, feeling completely refreshed, restored and relaxed.

        Mother and daughter looking relaxed and refreshed after spa treatments at the Spa at Palmer House.
        Mother and daughter looking relaxed and refreshed after spa treatments at the Spa at Palmer House, the perfect end to our trip and long days of volleyball. Photo credit: Emily Molina

        FAQs

        Where is the best place to stay for a volleyball tournament in Chicago?

        The Palmer House Hilton, located in downtown Chicago’s Loop, makes an ideal home base, close to major attractions and restaurants, with public transit nearby. Don’t forget the relaxing spa.

        Is it possible to fit sightseeing into a busy tournament schedule in Chicago?

        Yes, it is. Fit some fun in around your tournament wave (AM or PM). Free mornings or afternoons can be utilized to visit nearby attractions. Keep activities flexible and low-stress.

        Is the Chicago CityPASS worth it during a busy tournament weekend?

        Yes, CityPASS saves time and money on top attractions like the Shedd Aquarium, Skydeck Chicago and many other places you want to visit. It’s flexible for busy schedules; just be sure to make reservations in advance where required.

        What’s the easiest way to get around Chicago?

        The CTA (bus and ‘L’ train), rideshares, and walking are all convenient. Both buses and trains are budget-friendly. Walking is great for sightseeing.

        What must-try foods should I check out while I’m in Chicago?

        Don’t miss deep-dish pizza (Giordano’s), Chicago-style hot dogs, local coffee shops and fun brunch spots like Sugary Chicago or açaí bowl cafes downtown.

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        Emily Molina is a freelance writer and author originally from the Midwest. She is a former International Flight Attendant and military spouse with a love for the sea and history, which has led her to pursue new stories and adventures. Currently located in the PNW, her writing and content can be found in various publications, including South Sound Magazine, Northwest Travel & Life Magazine, Experience Cannon Beach, Visit Tacoma Pierce County, Arcadia Publishing, Showcase Magazine, South Sound Business, 425 Magazine, Northwest Yachting Magazine, 48North, South Sound Talk, and more. A proud member of North American Travel Journalists (NATJA), the Society of American Travel Journalists (SATW), and the International Food Wine & Travel Writers Association (IFWTWA) A passion for history and the sea, combined with a deep curiosity about people, draws her to historic places. While pursuing a story, she discovered the Odyssey, sparking a newfound love that inspired her not only to learn how to sail but to write her first book, Tacoma’s Tall Ship: The Extraordinary Journey of the Odyssey.
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