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
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

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A river with yellow boats, a bridge, and tall buildings.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

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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

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
฿3,754
฿4,463 total
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,314 reviews)
"Great location, serious service and sanitation failures. Rooms are dated, which could be charming. The TV has basic channels only, so bring a Chromecast or Roku. The in room tablet is useless; that money should have gone to the TVs. Room service never came. I ordered biscuits and gravy and pancakes. ..."

Reviewed on 25 Aug 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
฿4,377
฿5,204 total
31 Aug - 1 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
฿8,354
฿9,806 total
18 Sept - 19 Sept
includes taxes & fees
8.4/10 Very good! (2,442 reviews)
"It is located walking distance within the airport"

Reviewed on 25 Aug 2026

Hilton Chicago O'Hare Airport
See all 5,366 properties in Chicago
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.

Stay near popular Chicago attractions

An aerial view of a baseball stadium surrounded by urban buildings.
Photo by © City of Chicago

Wrigley Field

9.0/10 (11,704 reviews)
Step into baseball's living museum where ivy-covered walls and a hand-operated scoreboard create timeless charm. Experience the electrifying atmosphere of Cubs games in this century-old "Friendly Confines."
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A Ferris wheel and a carousel at a fairground.

Navy Pier

9.0/10 (24,140 reviews)
This historic Chicago waterfront landmark offers panoramic lake views from its iconic Centennial Wheel. Enjoy seasonal fireworks or interactive exhibits at the Children's Museum while exploring Navy Pier.
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A large stadium surrounded by a cityscape with modern buildings.
Photo by © City of Chicago

Soldier Field

8.8/10 (7,063 reviews)
Soldier Field blends historic neoclassical columns with modern design as home to the Chicago Bears. Experience the electric atmosphere of an NFL game or take a guided tour exploring its century of sporting heritage.
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A modern cityscape with tall buildings, a clear sky, and a tree-lined street.
Photo by © Cesar Russ Photography

McCormick Place

8.8/10 (9,822 reviews)
McCormick Place hosts major events like the Chicago Auto Show in its 2.6 million square feet of exhibition space. Arrive via the convenient Metra Electric Line station directly beneath the complex.
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A river with boats, surrounded by tall buildings and a clear sky.

Chicago Riverwalk

9.6/10 (13,574 reviews)
This 1.25-mile urban promenade showcases Chicago's stunning architecture alongside the river. Stroll past public art installations, dine at waterfront cafés, or catch the evening Art on theMART digital projection show.
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A roller coaster in motion against a clear blue sky.

Six Flags Great America

8.6/10 (992 reviews)
This Midwest thrill-seeker's paradise boasts 15 roller coasters and immersive themed areas. Arrive at opening to conquer popular rides, or consider a Flash Pass to maximise your adventure.
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A cityscape with modern skyscrapers and the Cloud Gate sculpture.

Millennium Park

9.4/10 (30,446 reviews)
Discover Chicago's artistic heart at Millennium Park, home to the reflective Cloud Gate and interactive Crown Fountain. Stroll through Lurie Garden or catch a free concert at the Jay Pritzker Pavilion.
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A large, modern building with a curved facade and multiple vertical windows.

United Center

8.8/10 (4,269 reviews)
Home to the Chicago Bulls and Blackhawks, United Centre electrifies with championship energy and passionate crowds. Arrive early to see the iconic Michael Jordan statue before experiencing Chicago's premier sports venue.
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What to do in Chicago

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

฿893
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

฿1,559
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Art Institute of Chicago

Art Institute of Chicago

฿1,324
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago

Frequently asked questions

How much does a Chicago holiday package cost?
You'll find cheap prices on Expedia for your Chicago escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your holiday to Chicago costs.
What are the cheapest months to go to Chicago?
December, January and February are the best times to look for cheap Chicago holiday packages. Opting to travel in quieter periods means you'll typically find lower prices on accommodation and flights.
How many days is enough for Chicago?
To fully enjoy a Chicago holiday, we recommend booking for 2 days. Divide your time between visiting Michigan Avenue, Chicago Riverwalk and other well-known attractions, on top of experiencing neighbourhoods like Central Chicago and Near North Side. If you've got some spare time, include a day trip or tour in your Chicago holiday itinerary.
Is it worth booking a holiday package to Chicago?
Chicago has everything you need for a fantastic trip — views, dining and culture are just the start. Whether you want to visit attractions like Navy Pier and Soldier Field, or take the road less traveled, you'll find plenty to do on your Chicago holiday.
How to find the best Chicago package deals?
Use Expedia's filters to find some great Chicago package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Chicago package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.
Is it cheaper to book a Chicago holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still have the freedom to create a customised Chicago holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Chicago?
Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Chicago break.
How to plan a trip to Chicago?
  1. Choose when to travel: Check your diary and get your bags packed. Your preferred season and the activities available will also help you decide when to escape to Chicago.
  2. Set a budget: Factor in costs like flights, transportation and food when working out how much to put aside for your trip to Chicago. Then, choose a property that suits your budget, whether that's an affordable stay or a swankier getaway.
  3. Work out your trip length: Consider how long you'd like to spend discovering Chicago. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Chicago holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.