A river with a yellow boat, surrounded by tall buildings and a bridge.

Chicago Vacations from ¥350,461

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The Latest Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Oct 1 - Oct 5

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (4,883 reviews)
    Roundtrip Tokyo (TYO) - Chicago (ORD)
    NRT - ORD1 stop ORD - NRT1 stop
    ¥448,708
    ¥350,461
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • Sep 17 - Sep 21

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (542 reviews)
    "Comes with all the comforts of Home."
    Reviewed July 29, 2026
    Roundtrip Tokyo (TYO) - Chicago (ORD)
    NRT - ORDNonstop ORD - NRTNonstop
    ¥450,352
    ¥354,223
    per traveler
    found 1 day ago
    Level Chicago Fulton Market
  • Sep 17 - Sep 21

    Level Chicago - River North + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,042 reviews)
    "This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities"
    Reviewed July 30, 2026
    Roundtrip Tokyo (TYO) - Chicago (ORD)
    NRT - ORDNonstop ORD - NRTNonstop
    ¥448,761
    ¥366,051
    per traveler
    found 1 day ago
    Level Chicago - River North
  • Oct 6 - Oct 9

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,142 reviews)
    "Wonderful stay. O"
    Reviewed July 31, 2026
    Roundtrip Tokyo (HND) - Chicago (ORD)
    HND - ORDNonstop ORD - HND1 stop
    ¥442,264
    ¥363,128
    per traveler
    found 2 days ago
    Pendry Chicago
  • Oct 6 - Oct 9

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,957 reviews)
    "Very excellent service"
    Reviewed July 31, 2026
    Roundtrip Tokyo (HND) - Chicago (ORD)
    HND - ORDNonstop ORD - HND1 stop
    ¥481,109
    ¥400,260
    per traveler
    found 2 days ago
    Trump International Hotel & Tower Chicago

Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
Learn more about 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

What to do in Chicago

Chicago Hotel Deals

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.