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If You Only Have A Weekend to Spend in Chicago

Aug 29, 2018
by Danny Brown

A fun, short and sweet lineup of things you can do and places to check out on a weekend is waiting for you in Chicago, IL, the Windy City. It’s perfect for those looking for a quick getaway to rejuvenate themselves and there’s nothing like good food, amazing parks, and artistic music to get the juice going. Since Chicago is one of the more affordable and artistically sophisticated cities in the region, it’s a dream ticket.

Chicago is the birthplace of modern architecture with many historical buildings converted into a modern, stylish living and working spaces that stays faithful to its roots. In the Great Lakes region of the American Midwest, the city experienced the biggest building boom known to the country's history. There are, hence, plenty of cloud-piercing buildings and lofty skyscrapers to admire, and a panorama of transformed historic buildings all-around.

The locals also have an undying and unshakeable optimism often brimming forth in the form of their infectious can-do spirit. Getting pumped with music, art, and history is the best way to take you into another world.

Chicago signboard in downtown IL
Source: Brad Knight at Unsplash

Modern Architecture and a World-Class Park

Without a smidgen of doubt, the best place to start your trip would be The Loop, Chicago’s central business district encircled by The L, the elevated train line. A striking sight to behold, the Willis Tower can’t be missed. It was the world’s tallest building for 25 years and offers a 60-second elevator ride up to the top for an unforgettable view of the city’s skyline, river, and waterways.

Formerly known as Sears Tower (the former name sometimes remains on the mouths of the locals; change is hard, as the saying goes), the Skydeck is on the 103rd floor of the building, making it the highest observation deck in the United States.

Using the Chicago CityPASS will get you into most major tourist attractions around Chicago, so purchase it and you’ll save yourself a lot of time and effort. 

The 40th annual @ChicagoJazzFestival has made its way to the park! Stop by 11a-9p today through Sunday! FREE!

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One reason over a million people visits the Skydeck every year is due to its awesome views, amenities for events, cafe, lounge and conference center. Since the building leans about 4 inches towards the west, placing an unequal load on its foundation, on windy days, you might even feel the building sway a little! Worry not, it’s perfectly safe, and they have designed it that way!

After taking in the views of the city, take the charter bus to Millennium Park which is a short drive away, well within The Loop’s vicinity. The attraction was planned well ahead of time to celebrate the welcoming of the third millennium. Together with Navy Pier, they are top attractions in Chicago! What you can see at Millennium Park is aplenty but taking the spotlight are artistic highlights like the Jay Pritzker Pavilion, Cloud Gate, the Crown Fountain and Lurie Garden. Its post-modern architectures and art installations are truly soothing for the soul.

And if time permits, don’t forget to attend a show at the Irving B. Harris Theater for Music and Dance, enjoy ice-skating at the McCormick Tribune Ice Skating Rink or visit the McDonald’s Cycle Center. When the sun is still up, snap a few pictures with The Bean, otherwise known as Cloud Gate, to update your family and friends on Instagram.

Going into the weekend like 📸: @apollo.dubs

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  • Willis Tower
    233 S Wacker Dr, Chicago, IL 60606
    (312) 875‐0066:
    Sales@theskydeck.com
    Hours: Daily 9am - 5pm
    www.willistower.com
  • Millennium Park
    201 E Randolph St, Chicago, IL 60602
    (312) 742-1168
    Hours: Daily 6am - 11pm


Wonderful Locations for Shopping, Dining and Drinks

Just slightly north of The Loop is the renowned Magnificent Mile. This is where you'll find countless historic buildings, architectural wonders that survived The Great Chicago Fire like The Old Water Tower (it might look just a teeny bit out of place but that’s what’s so charming about it), and the technological phenomena that is the Chicago School of Architecture.

Its wide, well-paved sidewalks are perfect for languid window-shopping even if you don’t have plans to splurge on the branded outlets here. Find a table at a quaint cafe nearby and people-watch over aromatic coffee and mouth-watering cakes and waffles! There will be shops like Neiman Marcus, Saks Fifth Avenue, Nordstrom, Barneys New York, Bloomingdale's Bulgari, Gucci, Louis Vuitton, Max Mara, Hugo Boss and many more waiting for you around the corner.

Dreamy days on #TheMagMile 📷: @rafwinterpacht

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The premier location is always bustling round the clock because it is home to posh hotels, luxurious restaurants, upscale establishments, tourist attractions and historic buildings. In fact, people stream in and out of the 100-story former John Hancock Center (renamed 360 Chicago) and its rooftop observation deck and fine diner till late. In fact, you’re encouraged to take on The Tilt, enjoy a multimedia presentation at the museum-style ground floor exhibit, and order a few rounds of delicious cocktails from the Bar at 360 Chicago. You can also take quick snapshots of buildings like Tribune Tower, the Allerton Hotel, Drake Hotel and Intercontinental Hotel from where you are.

Chicago: where every day, afternoon, night, angle is different. Come see them all from the 94th floor. #360chicago #chicago . . . #chitecture #mychicagopix #insta_chicago #artofchi #illgrammers #exploreillinois #abovechicago #passionpassport #chicagogram #chigram #wonderlust #flippinchi #chicagogrammers #instagood #cityscape #chi_shooters #wu_chicago #artofvisuals #way2ill #likechicago #theculturetrip #travelawesome #chicagohome #viewfromthetop #tlpicks #onlinechicago

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For a change of pace, bring the charter bus to the neighboring Riverwalk.


The activities found along the Chicago Riverwalk are centered on its waterways. It features the Chicago Cycleboats, Chicago Electric Boat Company, Chicago's First Lady Cruises, Chicago Water Taxi, Downtown Docks, Urban Kayaks, and the Mercury Skyline Cruiseline.

You can find the Art Institute of Chicago, the oldest and largest one of its kind in the United States, approximately a 5-minute drive from Magnificent Mile. As you take a stroll around the 264,000-square-foot museum, some stuff you’ll recognize at first sight, others will make you stop in your tracks to think. The collection and exhibits come from all around the world - Europe, North America and from all corners of Asia.

Pop by the eclectic, rustic and historic Chicago Athletic Association, a restored hotel with a gothic-style decor, you’ll be walking into a place where men shook hands over done-deals, celebrations held, games won and wine drank. It’s still a breathing ode to Chicago’s rich culture and history. Public figures used to roam, dine in, drank, played and venerable members enjoyed its exclusive amenities. Today, it is a highly regarded restored hotel along the Chicago Cultural Mile that offers panoramic views of downtown Chicago. Take your pick from 7 dining establishments on site which includes Cindy's Rooftop Terrace, Cherry Circle Room, and Game Room.

They, by the way, welcome walk-in, non-hotel-guests today.

best room services, hotels to stay in in Chicago IL
Source: Adi Goldstein on Unsplash

  • Chicago Riverwalk
    Chicago Riverwalk, Chicago, IL 60601
    (877) 300-6746
    Hours: Daily 6am - 11pm
    www.chicagoriverwalk.us
  • 360 Chicago (formerly known as John Hancock Center)
    875 N Michigan Ave, Chicago, IL 60611
    Hours: Daily 9am – 11pm
    www.360chicago.com
  • Art Institute of Chicago
    111 S Michigan Ave, Chicago, IL 60603
    (312) 443-3600
    Hours: Daily 10.30am - 5pm; Thur 10.30am - 8pm
    Admission: $25 for Adults, $20 for Residents of Chicago, $22 for residents of Illinois, $19 for Seniors, $19 for Students, $19 for Teens age 14 - 17, Free Admission for Children age 14 and younger
    Free Admission is given to residents of Illinois every Thursday from 5pm - 8pm all year round
    www.artic.edu
  • Chicago Athletic Association
    (312) 940-3552
    www.chicagoathletichotel.com


There’s Nothing Like Going Local

The 'When in Rome' saying is true: the best way to get to know another city is to hit the ground running and do what the locals do.

If you’re visiting Chicago at the end of the year, be sure to make a trip to the Christkindlmarket in Daley Plaza where souvenirs and decorative items are on offer at bargain prices. They would make perfect gifts for your family back home. The Christmas market is held only once a year and yet it attracts over a million visitors. At other times, you'll get to enjoy its majestic outdoor public space with a fountain for events, gatherings, and celebrations.

celebrate Chriatmas in Chicago IL
Source: chuttersnap at Unsplash

The list of unique Chicagoan cuisine to try is endless but we strongly recommend popping by Portillo’s to sink your teeth into delicious hot dog & chili, beef and sausage sandwiches, charbroiled burgers, ribs, shakes and more.

Hot Diggity Doug! Franks for stopping by, @itsdougthepug ❤️🌭

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Nobody does gourmet popcorn how Garrett Popcorn Shops does. They offer everything from Spicy Cheesecorn to Macadamia CaramelCrisp, Vulcan Cheesecorn to CaramelCrisp. They have (on the last count) 6 outlets located throughout Chicago and we’ve listed a few along The Loop and Magnificent Mile for you to check out.

And a simple search would reveal that one of the most sought-after dishes in Chicago is the famed deep-dish pizza! World-famous chef has spoken about and sung heaps of praises upon this wonderful dish and most locals would recommend trying it out at a nearby Giordano’s. Just check out their website, enter your location and they’ll direct you to the outlet closest to you!

🍿+🍺= the only way to do International Beer Day! Grab a Tin and a pint, and join us and @revbrewchicago in celebrating. Cheers!

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  • Richard J. Daley Center
    50 W Washington St, Chicago, IL 60602
    (312) 603-3054
    Hours: Mon to Fri 8am - 6pm
  • Portillo’s
    100 W. Ontario, Chicago, IL 60610
    (312) 587-8910
    Hours: Daily 10am - 1am
    www.portillos.com
  • Garrett Popcorn Shops
    - 625 North Michigan Avenue, Chicago, IL 60611
    - Millennium Park Plaza, 151 North Michigan Avenue, Chicago, IL 60601
    - 4 East Madison Street, Chicago, IL 60602
    (888) 476-7267
    www.garrettpopcorn.com
  • Giordano's
    1040 W Belmont Ave, Chicago, IL 60657
    (773) 327-1200
    Hours: Sun to Thur 11am - 11pm, Fri and Sat 11am - 12am
    www.giordanos.com

Places to Hang Out with the Whole Family

Navy Pier, the number one tourist attraction in Chicago, has held onto its top spot ranking for good reasons - it has everything for the entire family. There’s live entertainment, the best views of the Chicago cityscape and shoreline, a Ferris Wheel, lake and river cruises, and lots of space for a relaxing, calming evening.

Experience the beauty of the Pier at night. #AlloftheLights 😍 📷: @chreezy31

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Located a short distance south of Navy Pier are two of the most prominent and promising museums of all time - The Field Museum and the Museum of Science and Industry. Over 20 million specimens from all around the world are found at The Field Museum. This includes Sue, the world’s largest and most intact skeleton. If the museum looks familiar, it’s because it used to pop out of your movie screens in the form of Indiana Jones's dangerous escapades.

Approximately 10 minutes' drive away from The Field Museum is The Museum of Science and Industry, often called the "best field trip ever". This is where children are encouraged to unabashedly celebrate and explore creativity while their questions are indulged in. Its exhibits include The Story of Earth, Oceans: Our Blue Planet, Extreme Ice, Tornado Valley, Inspiring the Next Generation of Innovators, The Science Behind Pixar and Coal Mine. With the warm welcome, kids feel less shy and more inclined to throw their questions out towards the guides and teachers. THAT is learning.

Let your imagination fly. . . . . . 📸: @nancynb #msichicago #scienceofpixar #buzz #lightyear #summer #spaceranger #explore #curiosity

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While the Chicago History Museum gives you microscopic insights into just about every aspect of the city’s growth, traditions, and culture, Lincoln Park is so big that it covers neighborhoods like West DePaul, Old Town Triangle, Park West, and RANCH Triangle, just 15 minutes outside The Loop. There’s also 184-acres worth of space at Garfield Park Conservatory to enjoy with your entire family, complete with a fishing lagoon, athletic fields, tennis courts, a swimming pool, a stunning botanical garden and year-round environmental programs. It’s often referred to as a “landscape art under glass” and its outdoor garden is the real deal where children are accorded tons of space to splash and run around in.

It’s also super, SUPER romantic at night! Just saying.

Happy #NationalVolunteerWeek! We couldn't do it without them—volunteers bring skills, life experience, and energy to supporting CHM’s mission and the work of our staff. Their time and talent are an integral part of our success. To learn more about volunteering at CHM, visit chicagohistory.org/volunteer #chicagohistorymuseum

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Join us today for Beach & Dune Tinkerlab at Fiddleheads. Explore sand and water while we think about summer, the beach and how plants live at the shore. Get your hands dirty in some kinetic sand and enjoy our outdoor Play & Grow Garden! #DoAtGPC #playoutside #sensoryplay #natureeducation

A post shared by Garfield Park Conservatory (@gpconservatory) on


Before Frank Lloyd Wright became globally recognized in the world of design and architecture, he spent a significant number of years working on homes around Oak Park for local rich residents and getting a headstart working for the famous Sullivan & Adler firm. The historic district boasts of the world’s largest collection of homes designed by Wright which includes his own personal home and studio. It’s awesome just to get on the rented charter bus to take a slow cruise around Oak Park to view homes like Frank Lloyd Wright Home & Studio, Harry S. Adams House, William E. Martin House, Oscar B. Balch House, William G. Fricke House, Harry C. Goodrich House, Edward H. Cheney House, Rollin Furbeck House and the bootleg home of Thomas H. Gale House. There are many more where that list came from.

Amongst his many wonderful creations is Unity Temple, considered by many as one of Wright’s most important contributions to the Oak Park community. It was the world’s first modern building and Chicagoans are immensely proud of it! Being a working church, it is used on Sunday and closed for tours. So, if you wish to sign up for a self-guided audio tour, any other day would have to do.

Unity Temple, Chicago IL
Source: Creative Commons


  • Navy Pier
    600 E Grand Ave, Chicago, IL 60611
    (312) 595-7437
    Hours: Sun to Thur 10am - 10pm, Fri and Sat 10am - 11pm
    www.navypier.org
  • Field Museum of Natural History
    1400 S Lake Shore Dr, Chicago, IL 60605
    Hours: Daily 9am - 5pm
    Admission: $38 for Adults, $27 for Children age 3 - 11, $33 for Seniors age 65+, $33 for Students with ID; you'll get the most value with a CityPASS with a whopping half-price discount
    www.fieldmuseum.org
  • Museum of Science and Industry
    5700 S Lake Shore Dr, Chicago, IL 60637
    Hours: Daily 9.30am - 5.30pm
    www.msichicago.org
  • Chicago History Museum
    1601 N Clark St, Chicago, IL 60614
    (312) 642-4600
    Hours: Mon to Sat 9.30am - 4.20pm, Tues 9.30am - 9pm, Sun 12pm - 5pm
    Admission $19 for Adults, $17 for Seniors age 65+, $17 for Students age 19 - 22 with ID, Free Admission for Children age 18 and younger; Discounts and Free Admission also offered to Active US Armed Services, Chicago Police Department, teachers, pre-registered school field trips, park voyagers, Illinois residents, etc
    www.chicagohistory.org
  • Garfield Park Conservatory
    300 N Central Park Ave, Chicago, IL 60624
    (312) 746-5100
    Hours: Daily 9am - 5pm, except Wed 9am - 8pm
    Admission: Free Admission all year round, donations optional but encouraged
    www.garfieldconservatory.org
  • Unity Temple
    875 Lake St, Oak Park, IL 60301
    www.unitytemple.org

Enjoy the Best of Both Worlds in Chicago, IL

We’ve given you a few shortcuts, easy links, and suggestions for how to make the most out of your short weekend in Chicago in this article and we hope you enjoy your stay. It’s one of the most historically significant cities in the United States and we take pride in everything, from the oldest buildings to the most modern attractions in the city. Whether it is touring Wright's iconic buildings around Oak Park or sinking your teeth into unforgettable deep-dish pizza and hot dogs, we hope you'll be back for another day-trip, field trip, weekend family outing or a conference soon.

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renting a charter bus in Chicago IL affordably

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