Chicago Packages (Flight + Hotel)

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Where to stay in Chicago

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

Things to do in Chicago

Shopping

In Chicago, Woodfield Mall offers a vibrant shopping experience with a mix of high street brands and entertainment. For unique finds, visit the Afrocentric Bookstore. Gurnee Mills combines shopping and family-friendly activities, making it a fantastic spot for souvenirs and gifts.

Recreation

Wrigley Field offers an energetic atmosphere, perfect for sports enthusiasts looking to soak in the vibrant culture of Chicago. The Chicago Theatre provides a romantic setting for captivating performances, while Northerly Island Natural Area invites visitors to unwind with its peaceful landscapes and tranquil surroundings.

Adventure

Experience the thrills at Rainbow Falls Waterpark, where you can enjoy exhilarating water slides and family-friendly entertainment. For a dose of nostalgia and fun, head to Galloping Ghost, an arcadeAdventureZone filled with classic games. Finally, explore the scenic Salt Creek Trail, perfect for hiking amidst nature.

Nightlife

Experience Chicago's vibrant nightlife at Dave & Buster's, where you can enjoy drinks and entertainment in a lively pub atmosphere. For a taste of the city's rich music scene, visit Kingston Mines or Blues on Halstead, both offering romantic vibes and pulsating nightlife in the heart of the city.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Chicago

Chicago offers a delightful blend of family-friendly activities, outdoor adventures, and urban experiences, making it an ideal holiday destination. Explore vibrant urban parks, the esteemed modern colleges and universities, and engaging event venues. With a rich cultural scene and a variety of attractions, visitors can enjoy the city's unique charm, especially in the bustling downtown area.

  • Navy Pier: A vibrant hub of entertainment, Navy Pier offers stunning lakefront views and a variety of attractions including restaurants, shops, and the iconic Ferris wheel. It's an ideal spot for families and friends to enjoy the lively atmosphere and scenic surroundings.
  • Millennium Park: This expansive urban park is a must-visit, featuring the famous Cloud Gate sculpture and beautiful gardens. It serves as a fantastic venue for family outings, outdoor concerts, and art installations, all set against the backdrop of Chicago's stunning skyline.
  • Chicago Riverwalk: A picturesque promenade along the river, the Chicago Riverwalk invites visitors to explore charming cafes and enjoy leisurely strolls. Perfect for families, this area offers a unique perspective of the city, with beautiful bridges and waterfront activities.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudySlightly LowSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly LowAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyAverageSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighAverage
August73.0°F (22.8°C)Light RainMostly SunnySlightly HighAverage
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighSlightly High
October54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly High
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly Low

Tips to save on your trip to Chicago

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • 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.

Top hotels in Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ฿4,364 per night from 25 May to 26 May
฿4,364
฿5,188 total
25 May - 26 May
includes taxes & fees
8/10 Very Good! (10,134 reviews)
"Great location. Walkable to all the downtown attractions. Historical hotel with updated rooms. Highly recommend."

Reviewed on 23 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ฿7,809 per night from 16 Jun to 17 Jun
฿7,809
฿10,215 total
16 Jun - 17 Jun
includes taxes & fees
9.4/10 Exceptional! (4,221 reviews)
"The room is clean. The location is great with many nice shops nearby, including the Starbucks Reserve Roastery. It’s within walking distance to Navy Pier, Willis Tower, boat ride and many other architectural marvels. The breakfast is good with some variations each day. The staff are generally friendly ..."

Reviewed on 24 May 2026

Hotel Riu Plaza Chicago
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ฿2,836 per night from 25 May to 26 May
฿2,836
฿4,369 total
25 May - 26 May
includes taxes & fees
8.2/10 Very Good! (2,717 reviews)
"Too small room no refrigerator no microwave over prized vallet parking when they park in open public parking space which cost less."

Reviewed on 23 May 2026

Hotel Felix River North/Magnificent Mile
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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What to do in Chicago

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