Your Ultimate Guide to Exploring the Windy City

Discover the architectural marvels, world-class attractions, and vibrant culture that make Chicago one of America’s most captivating destinations. From its stunning skyline to its lively neighborhoods, this guide takes you through the must-see spots, hidden gems, and unforgettable experiences that define the spirit of Chicago. Find Things to Do in Chicago

1. Best Things to Do in Chicago
Your Ultimate Guide to
Exploring the Windy
City
Discover the architectural marvels, world-class attractions, and
vibrant culture that make Chicago one of America’s most captivating
destinations. From its stunning skyline to its lively neighborhoods, this
guide takes you through the must-see spots, hidden gems, and
unforgettable experiences that define the spirit of Chicago. Find
Things to Do in Chicago

2. Welcome to Chicago: The Windy City
Chicago stands as a magnificent testament to American innovation and culture, where
stunning architecture meets world-class arts and a thriving culinary scene. Known
affectionately as the "Windy City," this metropolitan powerhouse along Lake Michigan's
shores offers an unforgettable blend of urban sophistication and Midwestern warmth.
Whether you're exploring top attractions or discovering hidden gems, there’s no shortage
of amazing things to do in Chicago. To learn more about Chicago, dive into its rich history,
vibrant neighborhoods, and endless experiences that make this city truly one of a kind.
Quick Facts:
Population: 2.7 million (3rd largest U.S. city)
Location: Southwestern shore of Lake Michigan
Famous for: Architecture, deep-dish pizza, jazz heritage
Neighborhoods: 77 distinct communities
From its iconic skyline punctuated by architectural masterpieces to its 26 miles of
pristine lakefront, Chicago seamlessly blends natural beauty with urban energy,
making it an essential destination for any traveler.
www.mysittivacations.com

3. Must-See Attractions
Chicago's world-renowned landmarks offer something for every type of traveler, from art enthusiasts to architecture lovers and thrill-
seekers.
Millennium Park & Cloud Gate
Home to the iconic "Bean" sculpture, this
24.5-acre park features stunning public art,
gardens, and free concerts at the Pritzker
Pavilion.
Navy Pier
Chicago's premier entertainment destination
stretches 3,300 feet into Lake Michigan,
featuring rides, restaurants, gardens, and
spectacular fireworks.
Art Institute of Chicago
One of the world's greatest art museums
houses over 300,000 works, including Grant
Wood's "American Gothic" and Monet's
iconic water lilies.
Willis Tower Skydeck
Experience breathtaking 360° views from 1,353 feet up. Step
onto The Ledge, a glass box extending 4.3 feet from the
building—not for the faint of heart!
360 Chicago Observation Deck
Located on the 94th floor of the John Hancock Center, this
venue offers stunning lake and city views plus the thrilling TILT
experience—a moving glass platform.

4. Explore Chicago's Vibrant Neighborhoods
Each of Chicago's 77 neighborhoods has its own distinct personality, offering unique experiences from trendy boutiques to historic landmarks.
Lincoln Park
This affluent North Side neighborhood is home to the city's largest public park, a world-class zoo (free admission!), upscale shopping along
Armitage Avenue, and beautiful tree-lined residential streets. Perfect for families and outdoor enthusiasts.
Wicker Park
The epicenter of Chicago's creative scene, Wicker Park pulses with indie boutiques, vintage shops, craft cocktail bars, and innovative
restaurants. Its historic Victorian homes and street art make it endlessly Instagram-worthy.
South Loop
Situated just south of downtown, this rapidly evolving neighborhood offers easy access to Museum Campus, Grant Park, and the lakefront. It
combines modern high-rises with historic landmarks and features some of the city's best views.
Wrigleyville
Named after the iconic Wrigley Field stadium, this energetic neighborhood comes alive on game days. Beyond baseball, you'll find lively sports
bars, music venues, and a fun, youthful atmosphere that extends well into the night.

5. Premier Hotels in Chicago
From luxury riverside retreats to historic landmarks, Chicago's finest hotels offer impeccable service, stunning views, and world-class amenities.
1
The Langham Chicago
Location: Downtown, along the Chicago River
Price Range: $400-$700/night
Occupying floors 13-16 of a stunning Mies van der
Rohe skyscraper, The Langham exemplifies
modern luxury. Features include a Chuan Body +
Soul spa, river-view rooms with floor-to-ceiling
windows, and the acclaimed Travelle restaurant.
Perfect for sophisticated travelers seeking
contemporary elegance.
2
The Peninsula Chicago
Location: Magnificent Mile
Price Range: $500-$900/night
This five-star sanctuary on the Magnificent Mile
offers unparalleled service and amenities.
Highlights include a stunning rooftop terrace, spa
with semi-Olympic pool, in-room technology that
controls everything from curtains to temperature,
and the exquisite Shanghai Terrace restaurant.
The epitome of refined luxury.
3
LondonHouse Chicago
Location: Downtown, Michigan Avenue Bridge
Price Range: $300-$600/night
This historic building combines 1920s architecture
with contemporary design. The showstopper is
LH on 22, a tri-level rooftop bar in the building's
iconic cupola offering 360° city and river views.
Modern rooms feature deep soaking tubs and
smart TVs. Ideal for design-conscious travelers.

6. Getting to Chicago: Flight & Airport Guide
Major Airports
1 O'Hare International (ORD)
One of the world's busiest airports, located 17 miles northwest
of downtown. Serves as a major hub for United and American
Airlines, offering flights to over 200 destinations worldwide.
2
Midway International (MDW)
Smaller and more convenient, located just 10 miles southwest
of downtown. Primary hub for Southwest Airlines with excellent
domestic connections and shorter security lines.
1 Find the Best Flight Deals
Book 3-4 months in advance for summer travel or 2-
3 months for off-peak seasons. Tuesday and
Wednesday flights typically offer better rates. Set
price alerts on Google Flights or Hopper for your
preferred travel dates.
2 Getting Downtown
From O'Hare: CTA Blue Line train ($5, 45 min) or
shared shuttle ($35-40). From Midway: CTA Orange
Line ($3, 30 min) or rideshare ($25-35). Both trains
run 24/7 and connect directly to downtown hotels.
3 Pro Travel Tips
Apply for TSA PreCheck ($78/5 years) to breeze
through security. Download the CTA Ventra app for
seamless public transit payments. Consider the CTA
3-Day Pass ($20) if you'll be using trains and buses
frequently.

7. Chicago's Culinary Scene
From iconic deep-dish pizza to Michelin-starred fine dining, Chicago's food scene is among the world's finest. The city's diverse
neighborhoods serve up authentic flavors from every corner of the globe.
Deep-Dish Pizza
Lou Malnati's: The gold standard
since 1971, known for buttery crust
and vine-ripened tomato sauce. Try
"The Lou" with spinach mix.
Pequod's: Features a caramelized
cheese crust that's become
legendary among locals.
Fine Dining Excellence
Alinea: Three Michelin stars. Chef
Grant Achatz's molecular gastronomy
creates edible art. Prix fixe menus
from $395. Book 2-3 months ahead.
Girl & the Goat: Chef Stephanie
Izard's bold flavors and creative small
plates. Reservations essential.
Local Favorites
Italian Beef: Head to Portillo's or Al's
Beef for thin-sliced beef on Italian
bread, dipped in au jus. Order it "wet"
like a true Chicagoan.
Chicago-Style Hot Dog: An all-beef
frank with mustard, relish, onions,
tomatoes, pickle, sport peppers, and
celery salt on a poppy seed bun.
Never ketchup!
Foodie Tip: Explore the Chicago Food Planet Tours for insider access to hidden gems in neighborhoods like Chinatown, Little Italy,
and Pilsen. Tours run 3-4 hours and include 6-8 tastings from family-owned establishments.

8. Best Time to Visit & Essential Travel Tips
1
Spring (April-May)
Weather: 45-70°F, blooming flowers
Highlights: Fewer crowds, outdoor dining returns, Cherry blossoms at
Washington Park
Pack: Layers, light jacket, umbrella
2
Summer (June-August)
Weather: 70-85°F, perfect beach days
Highlights: Peak festival season, outdoor concerts, rooftop bars in full swing
Pack: Sunscreen, comfortable walking shoes, light breathable clothing
3
Fall (September-October)
Weather: 55-75°F, stunning foliage
Highlights: Ideal conditions, Chicago Marathon, harvest festivals, beautiful
autumn colors
Pack: Medium jacket, layers, comfortable shoes for walking
4
Winter (November-March)
Weather: 20-40°F, occasional snow
Highlights: Holiday decorations, ice skating, museum season, lower hotel rates
Pack: Heavy coat, warm boots, gloves, hat, scarf
Smart Travel Tips
Getting Around
Purchase a Ventra Card for seamless CTA train and bus travel ($3 per ride, $5 for day pass)
The Loop's "L" trains connect all major attractions efficiently
Divvy bike-share offers 30-minute rides for $3.30, with 600+ stations citywide
Ride-sharing is abundant but expect surge pricing during peak times
Safety & Etiquette
Stay aware in crowded tourist areas; keep valuables secure
Research neighborhoods before exploring; some areas are best visited during daytime
Tip 18-20% at restaurants, $2-3 per drink at bars
Download the CTA tracker app for real-time train arrivals

9. Start Planning Your Chicago Adventure
Experience the Magic of Chicago
From its stunning lakefront and world-class architecture to its legendary food
scene and vibrant neighborhoods, Chicago offers an unforgettable urban
experience unlike any other American city.
What makes Chicago special:
Architectural masterpieces from the world's greatest designers
26 miles of beautiful lakefront parks and beaches
77 unique neighborhoods, each with distinct character
Michelin-starred restaurants alongside iconic local eateries
World-class museums, theaters, and cultural institutions
Year-round festivals celebrating food, music, and arts
Whether you're seeking architectural tours, culinary adventures, outdoor
activities, or cultural immersion, the Windy City welcomes you with Midwestern
hospitality and urban sophistication.