Hamburger
The classic American hamburger is a grilled beef patty served in a soft bun, often topped with lettuce,...
Introduction
Chicago, set on Lake Michigan, blends striking architectural wonders and rich history in the heart of the Midwest. Founded in the early 1800s, it's a vibrant city famous for jazz, deep-dish pizza, and some of the world’s tallest skyscrapers. August brings warm, sunny days—perfect for outdoor adventures with friends.
Luxury travelers can soak up the energy at rooftop lounges like Cindy's, indulge in world-class dining, and sail on a private yacht along the lakefront. With lively summer festivals, designer shopping, and renowned museums, Chicago offers an unforgettable, upscale group getaway.
Customized for these preferences:
Travel StyleTravelling with friends
Dates01-08 August 2025
BudgetHigh budget
AccommodationHotel, apartment or house
Interests and Activities:
arts and culturefestivals and eventsgastronomysightseeing and toursoutdoor adventuresnightlife and entertainment
Not what you're looking for? Create Your Own Guide!
Key Facts
Location
Midwest, United States
Currency
United States Dollar (USD)
Religion
Christianity (dominant)
Population
2,716,000
Language
English, Spanish, Polish
Electricity
120V, 60Hz, Type A/B plugs
Time zone
UTCCentral Time (CT) (UTC-6)
Country code
+1
Internet access
High-speed broadband and 5G widely available
Climate
Humid continental, cold winters, warm summers
Map
Logistics
Chicago is easy to reach, especially for high-budget travelers. Fly into O'Hare or Midway International Airports, both offering plentiful direct flights. Private jets and first-class options are available for added comfort. Limousines and private car services provide seamless transit to downtown.
If you prefer scenic travel, take Amtrak’s luxury trains from major cities, or arrive via Lake Michigan on a private yacht. Charter buses and limo coaches suit large groups. In early August, expect warm, sometimes humid weather; occasional thunderstorms may cause minor travel delays, especially with flights. Always confirm bookings and weather forecasts in advance.
Weather
Chicago experiences four distinct seasons, with cold, snowy winters and hot, humid summers. Spring and fall bring milder weather, making them pleasant times to explore the city’s world-class arts and culture scene, vibrant festivals, and outdoor experiences along Lake Michigan.
From August 1 to August 8, temperatures typically range from the mid 70s to mid 80s °F (about 24–29°C), with high humidity and occasional thunderstorms. While severe weather such as brief heavy rain or lightning can occur, extreme events are rare. This warm, energetic period is ideal for sightseeing, food tours, summer festivals, and enjoying Chicago’s dynamic nightlife.
Food & Drink
Chicago is famous for deep-dish pizza (try Lou Malnati’s or Pequod’s), Chicago-style hot dogs, Italian beef sandwiches, and innovative steakhouses like Gibsons or RPM Steak. For a fine dining experience, Alinea and Girl & the Goat are top picks, while The Aviary offers creative cocktails in a chic setting.
Trendy neighborhoods like West Loop and River North are packed with lively bars, upscale rooftop lounges such as Cindy’s, and jazz clubs. Tipping is customary at 18–20% of the pre-tax bill. Most dietary restrictions are accommodated, as Chicago’s diverse food scene embraces global flavors and creative menus.
Reserve tables ahead, especially at renowned spots, and check for seasonal food festivals, such as Chicago Restaurant Week, for tastings and special prix-fixe menus.
Barbecue Ribs
Barbecue ribs are slow-cooked, tender cuts of pork or beef that are generously seasoned with a flavorful dry...
Macaroni and Cheese
Macaroni and cheese is a creamy, indulgent dish made with elbow macaroni pasta and a rich, cheesy sauce....
New York-style Pizza
New York-style pizza is characterized by its thin, hand-tossed crust, generous cheese topping, and a variety of classic...
Southern Fried Chicken
Southern fried chicken consists of juicy, tender pieces of chicken that are coated in a seasoned batter and...
Accommodation
For a luxurious friends’ trip, consider staying in downtown neighborhoods like the Loop, River North, or the Gold Coast—close to nightlife, dining, and major attractions. Top hotels such as The Langham, The Peninsula, and Four Seasons offer five-star amenities, rooftop bars, and spacious suites perfect for groups.
For a home-like stay, explore high-end apartments or penthouses through Airbnb or Plum Guide, particularly in neighborhoods like West Loop and Lincoln Park. Book early for August, as Lollapalooza (August 1-4) drives up demand, especially downtown. Consider booking directly through hotel websites or upscale booking sites like Tablet Hotels for exclusive perks and the best selection.
Itinerary
Kick off your journey with an exploration into Chicago’s illustrious arts and cultural scene, soaking in world-class architecture, renowned galleries, and captivating urban history with your friends.
Architecture River Cruise on the Chicago River
Experience Chicago's legendary skyline and architectural wonders on a luxury river cruise. Enjoy guided commentary detailing the city’s rich history and snap incredible photos from the water. Booking an evening cruise adds a magical city lights view!
Explore the Art Institute of Chicago
Marvel at iconic works by Monet, Van Gogh, and Grant Wood among many others at this world-class museum. Guided tours are available for deeper insights. Don’t miss the Modern Wing, and relax with your friends at the on-site café afterward.
Stroll through Millennium Park and Snap a Photo at 'The Bean'
Discover Chicago’s vibrant public art scene at Millennium Park. Pose with friends at the iconic Cloud Gate sculpture, enjoy Crown Fountain, and take in the cityscape. The park often hosts free summer concerts and festivals!
Chicago 3D Fireworks Cruise
INSTANT
Experience a getaway without leaving the city on this 3D Fireworks Cruise, departing Wednesdays and Saturdays from the Chicago Riverwalk every week during the summer months. Enjoy lively narration to the Chicago Harbor Lock and capture stunning photos of Chicago’s skyline. Then put on your complimentary “3D” glasses and enjoy a musical soundtrack as you take in an unbeatable view of a Chicago’s fireworks display from Lake Michigan!
Attractions
4.1 (204 reviews)
Chicago 3D Fireworks Cruise
INSTANT
Experience a getaway without leaving the city on this 3D Fireworks Cruise, departing Wednesdays and Saturdays from the Chicago Riverwalk every week during the summer months. Enjoy lively narration to the Chicago Harbor Lock and capture stunning photos of Chicago’s skyline. Then put on your complimentary “3D” glasses and enjoy a musical soundtrack as you take in an unbeatable view of a Chicago’s fireworks display from Lake Michigan!
From $52 USD
4.8 (1617 reviews)
Chicago Favorites Ultimate Food and Walking Tour
INSTANT
Free Cancellation
The perfect tour for first timers to Chicago or those who want to explore Chicago's famous foods along with the city's top attractions, all on one tour. Stroll the beautiful streets of downtown Chicago & taste the Windy City’s favorite eats! Bobby’s Bike Hike, whose food tours are ranked Top 10 in America (USA Today) & Top 20 in the world (Tripadvisor), offers this ultimate food & walking tour to explore the hard-working, salt-of-the earth foods Chicago made famous; a slice of deep-dish pizza, a Chicago-style hotdog, Italian beef, popcorn & brownies. Bobby’s expert guides will lead you through downtown Chicago’s most iconic landmarks; Millennium Park, State St, Chicago Theatre, Riverwalk, Michigan Ave, & the Wrigley Building, all the while explaining the tales from Chicago’s rich food-centric history. Enjoy your food tour & receive a bonus 2-hour FREE bike or kayak rental for each ticket bought, adding value to your experience. Bike along the Lakefront Trail or kayak on Lake Michigan.
From $85 USD
4.2 (109 reviews)
Lake Michigan Fireworks Cruise in Chicago
INSTANT
No city embraces summer quite like Chicago. Join in the celebration with friends and family on this epic fireworks cruise. Get up-close and personal every Wednesday and Saturday night with an unobstructed 360-degree view of this exciting and thunderous spectacle.
From $55 USD
4.7 (771 reviews)
Chicago Architectural River Cruise
INSTANT
Free Cancellation
Take in the views on this award-winning 90-minute Architectural Tour, a jaw-dropping excursion through a city that defies all expectations!
From $50 USD
4.9 (486 reviews)
Chicago's Chinatown Food and Walking Tour
INSTANT
Free Cancellation
Few neighborhoods in America combine such delicious cuisine with such fascinating history as Chicago’s Chinatown. Join Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in America by USA Today and Top 20 in the world by Tripadvisor, for an afternoon of interesting beats and scrumptious eats through Chinatown. On this 3-hour walking and food culture tour, you’ll see the bustling Chinatown Square, then get to sampling some of the richest cuisine around, including Cantonese dim sum, Portuguese-Chinese bakery treats, Szechuan style, and even Xi'an cuisine, all the while learning about the history of how these foods and cultures arrived in Chicago. This is a totally unique culinary tour experience, and not to be missed! Upon arrival to the tour, you can add a VIP Drink option for alcoholic and ethnic drink pairings! Chinatown can be challenging to navigate on your own, so let our expert guides show you the way and discover five of our all-time favorites.
From $80 USD
4.4 (499 reviews)
Chicago CityPASS®
INSTANT
Experience 5 must-see attractions and save up to 49% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax and enjoy your memories in the making. With 9 days to use your tickets, you’ll have plenty of time to explore the top sights. Chicago CityPASS® tickets include one-time admission to 5 attractions. Includes: • Shedd Aquarium • Skydeck Chicago Plus choose 3 of the following: • Shoreline Sightseeing Architecture River Tour • Field Museum • 360 CHICAGO Observation Deck • Griffin Museum of Science and Industry • Art Institute of Chicago • Adler Planetarium
From $142 USD
4.6 (29 reviews)
Chicago Premier Plus Brunch Cruise on the Chicago River
INSTANT
Sail along the magnificent skyline on our Premier Plus Chicago Brunch Cruise. A chef-curated menu of plated brunch specials will delight your palate while unparalleled panoramas of the city’s iconic architecture are marveled at from our glass-enclosed vessel. Enjoy the awe-inspiring views of landmarks such as the Willis Tower, Navy Pier, and the Old Chicago Post Office in the comfortable interior or from the open-air spaces. This upscale experience on the Chicago River is complete with bottomless mimosas and a fully stocked cash bar, light architectural narration, masterful DJ entertainment, and exceptional service. Elevate your weekend with an unforgettable afternoon brunch cruise against a backdrop of Chicago’s most spectacular scenery.
From $110 USD
FAQ
Find quick answers to your Chicago travel questions with our travel guide chatbot. Your questions will be added to this section to help other travellers.
Travel Essentials
Expedia
Holiday Homes, Hotels, Car Rentals, Flights
Special Offer:
Members save 10% or more on over 100,000 hotels worldwide
Wise
Best multi-currency travel debit card
Special Offer:
Get a free card or zero fees on a transfer up to SGD 900
Airalo
Travel eSIMs for data in 200+ destinations
Special Offer:
15% off an eSIM
NEWTOAIRALO15
Hotels.com
100,000+ Places to Stay, for Every Style & Budget
Special Offer:
Loyalty Program: Stay 10 nights, get 1 free
Global Rescue
Medical, Security Evacuation & Field Rescue
Special Offer:
From US $139 for 7 days cover
Related Guides
View Guide
United StatesNew Jersey
1 days
Plan an unforgettable summer 2025 family getaway to New Jersey with our family-friendly travel guide!
summer
View Guide
View Guide
United StatesHouston
4 days
Discover the ultimate 4-day solo travel itinerary for Houston in Summer 2025. Explore top sights, local tips, and create your own adventure.
summer
View Guide
View Guide
United StatesHouston
4 days
Embark on a summer 2025 solo adventure to Houston and use our guide to create unforgettable memories on your own terms!
summer
View Guide
View Guide
United StatesHouston
2 days
Set off on a solo journey to Houston! This 2-day Summer 2025 guide helps you explore, unwind, and make the trip your own.
summer
View Guide
Ready to plan your trip?
Share your travel insights or create a new guide for fellow adventurers!