The Premise: Forget faking a fever. Today, we’re leveraging the power of online booking and savvy scheduling to achieve the impossible: a perfect Chicago day. We’ll capture the essence of Ferris’s carefree spirit, but with a touch of modern efficiency.
We’re recreating the magic of Ferris’s legendary day, blending the classic movie moments with a modern Chicago experience.
The Itinerary:
Rise and Shine (But Not Too Early): 9:00 AM
Unlike Ferris’s elaborate setup, we’re relying on a well-charged phone and a killer playlist.
“Anything is peaceful from one thousand, three hundred and fifty-three feet.”
Take some epic panoramic photos for your social media.
Location: 233 South Wacker Drive, Chicago, IL 60606
Chicago Board of Trade: 1:00 PM
See the iconic building featured in the film.
Location: 141 West Jackson Boulevard, Chicago, IL 60604
Lunch at Italian Village: 1:45 PM
See the Iconic neon sign that was shown in the movie.
Location: 71 West Monroe Street, Chicago, IL 60603
Parking Garage & Wells Street: 2:30 PM
See the parking garage where the Ferrari was dropped off.
See Wells Street where the Ferrari joyride began.
Location: 172 West Madison Street, Chicago, IL 60602, and West Madison Street & South Wells Street, Chicago, IL 60602.
Art Institute of Chicago: 3:15 PM
Just like Ferris, Sloane, and Cameron, we’re hitting the Art Institute.
Modern Twist: Pre-book your tickets online to skip the lines. (Official Site: Art Institute of Chicago)
“A man needs a hobby.” We’ll soak in the art, especially Seurat’s “A Sunday on La Grande Jatte.”
Capture the moment with a quick, artistic Instagram reel.
Location: 111 South Michigan Avenue, Chicago, IL 60603.
Art Institute of Chicago – Iain Croll
Daley Plaza & Federal Center: 4:30 PM
Experience the Von Steuben Day Parade atmosphere (or a similar event).
See the Picasso sculpture.
Walk through the Federal Center and see the Calder’s Flamingo sculpture.
Location: 50 West Washington Street, Chicago, IL 60602, and 230 South Dearborn Street, Chicago, IL 60604.
Wrigley Field: 5:30 PM
A quick trip to Wrigleyville to soak in the atmosphere of Wrigley Field.
Even if there is not a game, the area is full of energy.
Take some photos of the iconic stadium.
Soak in the atmosphere of the iconic ballpark.
Location: 1060 West Addison Street, Chicago, IL 60613.
Lake Shore Drive: 6:30 PM
Cruise down Lake Shore Drive, enjoying the city skyline and lake views.
Location: 1114 North Lake Shore Drive, Chicago, IL 60611
Glencoe Beach: 7:30 PM
Cruise down Lake Shore Drive, enjoying the city skyline and lake views.
Location: 1114 North Lake Shore Drive, Chicago, IL 60611
Evening Views: 9:00 PM
Find a rooftop bar or scenic spot to enjoy the city lights.
Key Elements:
Respect for private property: When visiting residential locations, maintain a respectful distance.
Flexibility: Be prepared to adjust the itinerary based on traffic and event schedules.
Pre-plan: Book tickets and make reservations in advance, especially for popular attractions.
This itinerary provides a comprehensive tour of Ferris Bueller’s Chicago, blending movie nostalgia with the city’s modern attractions but it is just a framework. Feel free to customise it to your interests and preferences. Remember, the most important thing is to have fun and create unforgettable memories!
Is it achievable? Absolutely not this is for fun!
Where to Stay
🏳️🌈 About Cramberts
From our home base in Amsterdam, we frequently explore some of Europe’s most vibrant cities, and we’ve compiled detailed guides to share our insider knowledge. Whether you’re seeking the canals and culture of Amsterdam itself, the sunny beaches of Gran Canaria, the historic charm of Lisbon and Porto, the bustling energy of Barcelona and Madrid, the refined elegance of Paris and Munich, the unique character of Sitges, or the diverse landscapes of the Randstad region, you’ll find comprehensive information and recommendations in the links below.
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We love Chicago and have some amazing friends who live here. We’ve visited in the snow and in the summer and it doesn’t matter when you visit you’ll have an amazing time. Most of our friends have moved from Boystown to Andersonville in the last decade but both still have a lot to offer and of course the Loop for museums and culture.
Chicago, a city that embodies the spirit of “razzle dazzle,” lives up to its theatrical namesake. Reborn from the ashes of the Great Chicago Fire, this metropolis transformed itself into a beacon of culture and innovation, notably with the 1893 World’s Fair, a testament to its resilience and forward-thinking vision. Architect Daniel Burnham’s transformative designs sculpted Chicago into the modern marvel it is today, leaving an indelible mark on its urban landscape.
Today, Chicago’s reputation extends far beyond its architectural grandeur. It’s a culinary powerhouse, celebrated as America’s “Best Restaurant City” by Condé Nast Traveler, offering a diverse gastronomic experience that transcends its iconic deep-dish pizza and hot dogs. The city’s cultural richness is equally impressive, with the Art Institute of Chicago earning global acclaim as a top-tier museum.
Beyond its urban allure, Chicago offers an unexpected escape with 18 miles of pristine lakefront beaches. A stroll from Michigan Avenue’s upscale boutiques leads to the serene shores of Lake Michigan. Grant Park, a sprawling green oasis, further enhances the city’s appeal, providing a tranquil retreat amidst the urban bustle. Chicago, a city of contrasts and vibrant experiences, truly stands alone.
Gay Bars and Clubs in Chicago
While Boystown and Andersonville are the primary hubs of Chicago’s LGBTQIA+ nightlife, the Loop, Chicago’s central business district, has a significantly smaller and much less concentrated gay bar scene. The Loop is primarily a business and theatre district, and its nightlife tends to cater to a broader audience.
So you will want to head to Boystown (North Halsted) or Andersonville (where the gays all seem to be moving to now) and if you are visiting friends they are likely in one of these neighbourhoods anyway.
I’ve had the pleasure of visiting almost every LGBT venue in Chicago thanks to the annual pub crawl. The Thanksgiving Eve gay pub crawl in Chicago’s Boystown marks the unofficial kickoff to the holiday season. This pub crawl, a vibrant display of community spirit, provides a fun prelude to Thanksgiving.
Sidetrack
Show tunes and adult slushies? What’s not to like! This spacious video bar has numerous areas and spots to chat and mingle. Themed nights often feature drag shows and music videos on enormous screens. You’ll find a diverse crowd here, and the rooftop bar and patio is a must-see in the summer. Over the decades this bar seems to have taken over the entire block and it’s no surprise why.
The NorthEnd is a long-standing neighborhood gay bar with a relaxed and comfortable atmosphere. It’s a popular spot for locals and visitors alike, offering a friendly place to grab a drink, socialize, and enjoy a laid-back evening. With its unpretentious vibe and welcoming staff, The NorthEnd is a perfect choice for those seeking a casual gay bar experience. I think we visited for a decade before we discovered there was a second half to the bar LOL.
Indulge in a glamorous evening at Kit Kat Lounge & Supper Club, where the Kit Kat Divas deliver nightly performances every 20 minutes. This entertainment hotspot boasts an extensive martini and cocktail menu, featuring over 200 options, alongside upscale contemporary cuisine.
Located in the heart of Boystown, Hydrate offers a contemporary and energetic atmosphere. With a lineup of DJs and themed nights, this popular club keeps the party going until 4 or 5 a.m. on weekends.
Step into The Closet, a Boystown institution since 1978. While known as a lesbian bar, it welcomes all, fostering a diverse and inclusive environment. With an extensive drinks menu and pretty pink/purple lighting, it’s an ideal date spot.
Bobby Love’s brings a lively, retro vibe to Boystown. This bar is known for its energetic atmosphere, friendly staff, and a mix of music that keeps the dance floor moving. Expect themed nights, drink specials, and a welcoming crowd that’s ready to have a good time.
A Chicago staple since 1987, Roscoe’s Tavern offers the best of both worlds: a neighborhood bar vibe in the front and a large dance floor in the back. Check their calendar for regular drag shows and special events, including appearances by RuPaul’s Drag Race alumni.
A modern-styled space with two side bars and a dance floor boasting yet another bar, all staffed by attractive bartenders. Enjoy EDM beats from the DJ, colorful lights, and reasonably priced drinks at this new Boystown hangout.
Experience a no-attitude nightclub featuring alternative electronic music that draws an eclectic crowd. Open until 4 or 5 a.m. on weekends, it’s best to arrive early to avoid long lines.
One of Chicago’s oldest and first Black-owned gay bars, Jeffery Pub remains lively and modern. Enjoy live entertainment, drag shows, karaoke nights, Silky Soul Sundays, and DJs spinning everything from pop to house music. Note: Patrons must be 30 or older.
One of the few gay bars downtown, this unpretentious, old-school bar features a disco ball and divey digs that draw a mixed crowd of travelers and locals. Remember, it’s cash-only.
157 E Ohio St, Chicago, IL 60611
Scarlet
A vintage-inspired bar and lounge with a club atmosphere, themed nights, and special events. The DJs and drink specials attract a 20-something crowd ready to dance the night away.
With locations in both Boystown and Andersonville, this fancy cocktail bar is perfect when you’re craving something more sophisticated than a vodka soda. Enjoy carefully crafted drinks like a signature martini and weekly specials.
Boystown: 3452 N Halsted St, Chicago, IL 60657
Andersonville: 1509 W Balmoral Ave, Chicago, IL 60640
A towels-optional private men’s gym, sauna, and bathhouse. Memberships start at $8, and the facility offers many amenities, including private rooms, slings, whirlpools, and showers for gay and bi men looking for a playful time.
Described as “the kinky side of Boystown,” this bar lives up to that description, being especially popular with the leather crowd. The blacked-out windows and industrial look give it that kinky vibe, but it’s also just a lot of fun, even if you aren’t there for some sexy action. There’s a pool table and multiple dart boards to keep you entertained as you drink. They also hold themed kink nights for those looking to play in their own way, ranging from leather to neon nights.
The main event is the Pride Parade, which usually takes place on the last Sunday of June, with a route stretching from Montrose to Diversey on the North Side. The Saturday morning before is the annual Proud to Run 10k run and 5k walk, benefiting several community organizations. Festivities really begin the weekend before the parade, as the Pride Street Festival kicks off the week-long celebration. Pride-related events can be found throughout the city during the entire month of June. Even downtown and in the financial district, businesses and large institutions proudly fly the rainbow flag.
Pride Parade: June 29, 2025 (Expected – last Sunday in June)
This is the largest outdoor street festival in the Midwest, with attendance of over 200,000. It covers six blocks of North Halsted right in the center of Boystown, with five stages and a non-stop lineup of live music, food, and craft vendors. Think of it as an unofficial Pride Part II, taking place on one of the first weekends of August. Attendees aren’t afraid to express themselves with colorful outfits, and the drag queens are fierce.
August 9-10, 2025 (Expected – first weekend of August)
Located on West Randolph, Chicago’s renowned “restaurant row,” Au Cheval has garnered international acclaim for its exceptional burgers. This bustling diner-style spot operates on a first-come, first-served basis, so expect a wait, especially during peak hours. However, the reward is a culinary experience that many consider to be among the best in the world. Beyond their famous burgers, Au Cheval offers a diverse menu of classic diner fare with a gourmet twist.
Located in the heart of Boystown, Wood is a culinary gem named after its authentic wood-fired oven. This restaurant is a local favorite, particularly for its vibrant Sunday brunch and creative craft cocktails. The warm, inviting atmosphere and meticulously crafted menu make Wood an ideal spot for a leisurely meal or a lively gathering. woodchicago.com 3335 N Halsted St, Chicago, IL 60657
American Gothic at Art Institute of Chicago – Iain Croll
Day Trips / Architecture / Culture in Chicago
Frank Lloyd Wright Home and Studio
Oak Park, Illinois, a picturesque suburb easily accessible from Chicago via the “L” train, stands as a testament to the architectural genius of Frank Lloyd Wright. This charming town boasts one of the largest concentrations of Wright-designed homes in the United States, offering a unique opportunity to delve into the Prairie School movement. Wright himself resided in Oak Park for the first two decades of his career, a period during which he honed his distinctive style, characterized by horizontal lines, open floor plans, and a harmonious integration with nature.
Visitors can explore a remarkable collection of his creations, including the Frank Lloyd Wright Home and Studio, a National Historic Landmark. This site served as Wright’s personal residence and creative laboratory, providing invaluable insights into his design process and architectural philosophy. The meticulously preserved spaces showcase his innovative use of materials and his commitment to crafting environments that reflected the American spirit.
Beyond its architectural significance, Oak Park offers a delightful suburban experience with tree-lined streets and a welcoming atmosphere. Guided walking and bicycle tours provide in-depth explorations of Wright’s masterpieces, allowing visitors to appreciate the intricate details and enduring legacy of his work.
Embark on an unforgettable journey through Chicago’s architectural history with the Chicago Architecture Center River Cruise. This 90-minute tour, led by expert docents, navigates the Chicago River, providing unparalleled views of the city’s iconic skyline. From historic landmarks to contemporary skyscrapers, you’ll gain insights into the design and engineering marvels that have shaped Chicago’s urban landscape. Discover the stories behind renowned buildings, learn about the architects who envisioned them, and appreciate the city’s evolution from a trading post to an architectural powerhouse. This cruise is an essential experience for anyone seeking to understand and appreciate the Windy City’s architectural legacy.
111 E Wacker Dr, Chicago, IL 60601 (Departure point at the Chicago Architecture Center)
Frank Lloyd Wright left an impressive architectural legacy in Chicago and its surrounding areas. Here’s a list of notable Frank Lloyd Wright buildings in and around Chicago:
In Chicago:
The University of Chicago’s Robie House:
A masterpiece of the Prairie School style, known for its horizontal lines and open floor plan.
This itinerary follows the general sequence of the movie, but you can adjust it based on your interests and time constraints. There is literally no way to do all of this in one day but then what did you expect?
Cameron’s House (Exterior View):
Start your day with a glimpse of Cameron Frye’s modernist glass and steel home.
370 Beech St, Highland Park, IL 60035 (This is a private residence, so please be respectful and view from the street only.)
This is a bit outside of Chicago, but if you have a car, it is worth the detour.
Shermer Northbrook High School (Exterior View):
Where Ferris “attends” school.
2300 Shermer Rd, Northbrook, IL 60062 (Exterior view only, this is a functioning school)
Downtown Chicago:
Head into the loop/centre of Chicago.
The Art Institute of Chicago:
Recreate the iconic scene where Ferris, Cameron, and Sloane admire Georges Seurat’s “A Sunday on La Grande Jatte.”
Grab a classic Chicago-style hot dog for a quick and authentic lunch. Several vendors are located throughout downtown.
Chicago Board of Trade (Exterior View):
Pass by the Chicago Board of Trade building, where Ferris and his friends observe the trading floor.
141 W Jackson Blvd, Chicago, IL 60604
Parade Scene (Dearborn Street):
Walk along Dearborn Street, where Ferris commandeers the parade and sings “Twist and Shout.”
Dearborn Street, between Adams and Monroe.
Wrigley Field (Exterior View):
Although they don’t enter the stadium, they pass by it.
1060 W Addison St, Chicago, IL 60613.
Cameron’s Garage (Replica):
The garage scene was filmed on a sound stage, but if you want to see a very close replica, The Volo Auto Museum has a recreation of the garage, and the ferrari used in the film.
Transportation: Chicago has excellent public transportation (“L” train and buses). Consider purchasing a Ventra card for easy travel. Some locations, like Cameron’s house, are best reached by car.
Time Management: This itinerary is packed. Prioritize the locations that are most important to you.
Respect Private Property: Cameron’s house is a private residence. Please be respectful and view from the street only.
Check for Closures: Verify the operating hours and any potential closures of the attractions you plan to visit.
Wrigley field is a functioning stadium, and tours and games are scheduled. Check the cubs website for more information.
There is also a more ambitious itinerary if you really want to try to cram everything Ferris, Sloane, and Cameron did on the iconic day off!
Willis Tower (Skydeck Chicago)
Ascend to the iconic Willis Tower, formerly known as the Sears Tower, and experience breathtaking panoramic views of Chicago from the Skydeck. Located 1,353 feet in the air, the Skydeck offers unparalleled vistas of the city skyline, Lake Michigan, and beyond. Dare to step onto The Ledge, glass boxes extending from the building’s facade, providing a thrilling perspective of the city below. I say thrilling but yeah I was not a fan.
Welcome to Chicago’s lively LGBTQIA+ hub, Boystown, a vibrant neighborhood synonymous with queer culture and celebration. Nestled along North Halsted Street, this welcoming enclave beckons travelers seeking an inclusive and energetic atmosphere. Stroll down its bustling avenues, lined with an array of gay bars, dance clubs, and restaurants, each radiating its own unique charm. Experience the pulsating nightlife at iconic venues like Sidetrack and Roscoe’s, or savor a relaxed afternoon at one of the many outdoor cafes. For a unique experience, explore the themed nights and drag performances that define Boystown’s entertainment scene. You can find more of the many locations by exploring online maps, which are frequently updated. (ORD, MDW)
Transportation & Airport Transfers
Chicago boasts the United States’ second-largest public transportation system, operated by the Chicago Transit Authority (CTA), providing an efficient way to navigate the city and its 35 surrounding suburbs. The CTA’s expansive network of “L” trains and buses makes getting from point A to point B relatively seamless.
CTA fares are fixed per ride, regardless of destination. A single “L” train ride costs $2.50, and a bus ride is $2.25. While buses accept exact cash fares, they cost $2.50. CTA tickets and passes are managed through Ventra. A single-ride ticket, which includes up to two transfers within two hours, can be purchased at most CTA stations. Alternatively, a $5 Ventra Card allows you to load funds or purchase 1-Day, 3-Day, 7-Day, or 30-Day passes.
For detailed CTA fare and ticket information, visit the CTA website. To learn more about the Ventra card and app, visit the Ventra website.
Beyond public transit, rideshare apps like Lyft and Uber are widely available in Chicago and its suburbs.
For eco-conscious travelers, Chicago offers over 200 miles of on-street bicycle lanes. While dedicated lanes are increasing, most are shared with buses, requiring caution. For recreational cycling, the lakefront trail and the 606 are recommended. Divvy Bike provides bike rentals with numerous stations across the city.
Chicago is served by two major international airports: O’Hare International Airport (ORD), one of the world’s busiest, and Midway International Airport (MDW), more conveniently located.
The most cost-effective and efficient way to travel between the airports and downtown is via the “L” trains. The CTA Blue Line connects O’Hare to downtown, taking 40-45 minutes and costing $5. The Blue Line operates 24/7. The CTA Orange Line connects Midway to downtown, taking 20-25 minutes and costing $2.25. The Orange Line operates all day except for late-night and early-morning hours. During these times, the N62 Archer bus provides alternative transportation. Taxi fares range from $40-$50 from O’Hare and $25-$40 from Midway to downtown, depending on traffic and destination.
While car rentals are available at both airports, public transit, rideshares, and taxis are viable alternatives. Chicago is also accessible via Amtrak trains at Union Station and bus services like Greyhound and Megabus.
🏳️🌈 About Cramberts
From our home base in Amsterdam, we frequently explore some of Europe’s most vibrant cities, and we’ve compiled detailed guides to share our insider knowledge. Whether you’re seeking the canals and culture of Amsterdam itself, the sunny beaches of Gran Canaria, the historic charm of Lisbon and Porto, the bustling energy of Barcelona and Madrid, the refined elegance of Paris and Munich, the unique character of Sitges, or the diverse landscapes of the Randstad region, you’ll find comprehensive information and recommendations in the links below.
