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

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ฿7,706 per night from 26 Jul to 27 Jul
฿7,706
฿10,272 total
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,874 reviews)
"Convenient location and friendly staff."

Reviewed on 7 Jul 2026

Omni Chicago Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is ฿5,468 per night from 27 Jul to 28 Jul
฿5,468
฿6,501 total
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,711 reviews)
"They had extra charges, when checking in to my room. Also, the couch had stains in my room and only one of us could take a shower. The shower was plugged and filled up with water. Would not drain."

Reviewed on 8 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 ฿5,538 per night from 9 Jul to 10 Jul
฿5,538
฿6,585 total
9 Jul - 10 Jul
includes taxes & fees
8/10 Very good! (10,200 reviews)
"Dated hotel but the rooms are kept clean, updated flooring and really nice bedding. Fantastic location downtown, less than a mile walking distance from Museum Campus."

Reviewed on 7 Jul 2026

Congress Plaza Hotel
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

What to do 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.

Explore a world of travel with Expedia

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