Chicago Vacations from ￥94,232
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Chicago Vacation Packages
- River Hotel
Sep 25 - Sep 28River Hotel + Flight
Downtown Chicago3 nights4.0 star property8.8/10 - Excellent (5,322 reviews)"We loved our stay at the River Hotel in Chicago. The hotel was quiet and clean. The staff was very helpful. The hotel is in an excellent location in downtown Chicago, just steps away from the river and Michigan Avenue."Reviewed July 17, 2026Roundtrip • Los Angeles (LAX) - Chicago (ORD)LAX - ORD • Nonstop ORD - LAX • Nonstop￥126,192￥94,232found 3 hours agoper traveler - Fairmont Chicago at Millennium Park
Sep 25 - Sep 28Fairmont Chicago at Millennium Park + Flight
Downtown Chicago3 nights4.5 star property8.8/10 - Excellent (2,257 reviews)"Nice hotel. Very clean and well located"Reviewed July 15, 2026Roundtrip • Los Angeles (LAX) - Chicago (ORD)LAX - ORD • Nonstop ORD - LAX • Nonstop - Trump International Hotel & Tower Chicago
Sep 25 - Sep 28Trump International Hotel & Tower Chicago + Flight
Downtown Chicago3 nights5.0 star property9.6/10 - Exceptional (1,940 reviews)"Trump is the best in town for families. Staff is awesome and pool is great. Very walkable. We go every summer"Reviewed July 16, 2026Roundtrip • Los Angeles (LAX) - Chicago (ORD)LAX - ORD • Nonstop ORD - LAX • Nonstop - Silversmith Hotel Chicago Downtown
Sep 25 - Sep 28Silversmith Hotel Chicago Downtown + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (2,295 reviews)"The hotels biggest strength is it's employees. Thanks to all! And I understand the Silversmith will be under new owners on the fall. PLEASE keep your special employees!!! They are your strength. :)"Reviewed July 17, 2026Roundtrip • Los Angeles (LAX) - Chicago (ORD)LAX - ORD • Nonstop ORD - LAX • Nonstop￥139,510￥104,060found 3 hours agoper traveler - Kinzie Hotel
Sep 25 - Sep 28Kinzie Hotel + Flight
Downtown Chicago3 nights4.0 star property9.2/10 - Wonderful (2,163 reviews)Roundtrip • Los Angeles (LAX) - Chicago (ORD)LAX - ORD • Nonstop ORD - LAX • Nonstop￥138,546￥106,341found 3 hours agoper traveler
Where to stay in Chicago
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
West Loop
West Loop has transformed from industrial roots into Chicago's trendiest food destination. Old warehouses now house sleek restaurants along "Restaurant Row" where celebrity chefs create culinary magic. Art galleries and design studios fill converted brick buildings throughout this vibrant neighborhood. Union Park and Mary Bartelme Park offer green retreats amid the urban landscape. Getting around is simple with multiple train stations including Racine and Clinton. The neighborhood balances its industrial heritage with modern luxury in this walkable food lover's paradise.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Discover the most popular places to visit in Chicago
Wrigley Field
Soldier Field
McCormick Place
What to do in Chicago
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Hotel Deals
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
Hyatt Place Chicago/River North
Hyatt Place Chicago/River North
The Allegro Royal Sonesta Hotel Chicago Loop
The Allegro Royal Sonesta Hotel Chicago Loop
Aloft by Marriott Chicago Mag Mile
Aloft by Marriott Chicago Mag Mile
Hotel 55 Chicago Downtown
Hotel 55 Chicago DowntownExplore a world of travel with Expedia
Book with confidence
Things to do in Chicago
Shopping
Your shopping experience in Chicago will be delightful. Visit Woodfield Mall for a variety of shops and entertainment options. Don't miss LEGOLAND® Discovery Center for unique gifts. Gurnee Mills offers great shopping with family-friendly vibes, ensuring a memorable experience as you explore this vibrant city.
Recreation
At Wrigley Field, immerse yourself in the energetic atmosphere of a baseball game and enjoy the lively sports community. For a touch of culture, the Chicago Theatre offers a captivating mix of performances that resonate with romance and family entertainment, perfect for a night out.
Experience the vibrant music scene at the House of Blues Chicago, where you can enjoy live concerts in a lively setting, surrounded by the rich sounds of various genres that promote relaxation and enjoyment.
Adventure
Experience the thrill of Pirates Cove Children's Theme Park with its arcadeAdventureZone, perfect for family fun. Splash into excitement at Rainbow Falls Waterpark, where adventure and entertainment await. For a scenic outdoor escape, hike the Salt Creek Trail and immerse yourself in Chicago's beautiful landscapes.
Nightlife
Experience the vibrant nightlife in Chicago at Blues on Halstead, a lively nightclub offering romance and entertainment. For a fun twist, visit Dave & Buster's, a drinking pub perfect for games and drinks. Don't miss Kingston Mines, another energetic nightclub brimming with city vibes and live music.
Find the best attractions in Chicago
Chicago is an ideal destination for families and outdoor enthusiasts, offering a mix of urban parks, modern universities, and event venues. Visitors can immerse themselves in the city's rich culture while exploring attractions like the iconic Chicago Riverwalk and the scenic Chicago River. Whether you're looking to discover the city's vibrant neighborhoods or enjoy family-friendly experiences, Chicago provides something for every traveler.
- Michigan Avenue: Experience the vibrant energy of Chicago along Michigan Avenue, known for its stunning architecture, high-end shopping, and bustling atmosphere. This iconic street offers a perfect blend of urban culture and city excitement.
- Navy Pier: Enjoy the urban charm and scenic views at Navy Pier, where you can stroll along the waterfront, indulge in local cuisine, and take part in family-friendly activities. The friendly vibe and beautiful lakefront make it a delightful destination.
- Millennium Park: Discover the beauty of Millennium Park, a family-friendly urban oasis featuring stunning art installations, lush gardens, and outdoor concerts. It's a perfect spot for relaxation and enjoying the dynamic city ambiance.
Best time to go to Chicago
The best time to visit Chicago is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.
Tips to save on your trip to Chicago
- Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chicago.
- Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Chicago.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.