Chicago Holidays from NZ$3,018

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The Latest Chicago Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Trump International Hotel & Tower Chicago
Level Chicago Fulton Market
The Langham, Chicago
Omni Chicago Hotel

Our guide on where to stay in Chicago

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

Chicago Holiday

Things to do in Chicago

Shopping

In Chicago, visit Woodfield Mall for a vibrant shopping experience with a mix of entertainment and family-friendly options. Don't miss Cabela's for outdoor gear and Wolff's Flea Market for unique souvenirs and local goods, all reflecting the city's lively atmosphere.

Recreation

Experience the vibrant energy at Wrigley Field, where the thrill of sports ignites the atmosphere. Enjoy live music at House of Blues Chicago, a perfect spot for entertainment lovers. For a touch of romance and culture, Vic Theatre offers an enchanting theatre experience that’s ideal for families and friends alike.

Adventure

At Galloping Ghost, immerse yourself in a massive arcade with retro games, perfect for all ages. Orbit Skate Center invites you to glide on skates in a vibrant atmosphere, while Chasers Laser Tag offers thrilling battles in a dynamic arena. Each venue guarantees family-friendly fun in Chicago.

Nightlife

In Chicago, immerse yourself in vibrant nightlife at Dave & Buster's for a lively pub experience, or dance the night away at Blues on Halstead and Kingston Mines, both renowned nightclubs that offer a mix of romance and city vibes, perfect for an unforgettable evening out.

*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 fantastic blend of family-friendly outdoor activities and urban experiences, making it ideal for a diverse vacation. Explore urban parks, modern universities, and event venues while immersing yourself in the city's rich culture. Be sure to check out attractions like the Chicago skyline, discover local gems, and consider the Chicago CityPASS for convenient access to top sites.

  • McCormick Place: As one of the largest convention centres in the USA, McCormick Place offers a dynamic atmosphere for business events and expos. Experience the cutting-edge facilities and diverse events that attract visitors from around the globe, making it a hub of innovation and networking.
  • Navy Pier: This iconic jetty features stunning views of Lake Michigan and the Chicago skyline. Enjoy a vibrant mix of attractions, including restaurants, shops, and the famous Ferris wheel. It's a perfect spot for relaxation and socialising with friendly locals.
  • Millennium Park: A beautifully designed urban park, Millennium Park is ideal for families seeking outdoor fun. Home to the famous Cloud Gate sculpture and lush gardens, it’s a cultural hub where art and nature meet in the heart of the city.

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.

Our pick of the best Chicago Hotel Deals

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 NZ$278 per night from 29 June to 30 June
NZ$278
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,228 reviews)
"Housekeeping did not come a single time in the four days and four nights I stayed there. The beds were not made nor was the trash taken out a single time . I had to phone them twice to receive bath towels. I was using Uber eats take out bags as trash bags due to the lack of housekeeping not ..."

Reviewed on 9 June 2026

Congress Plaza Hotel
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is NZ$312 per night from 28 June to 29 June
NZ$312
28 June - 29 June
includes taxes & fees
8.8/10 Excellent! (2,638 reviews)
"Upsetting that I was given a room that I had to haul all of my luggage up 16 steep stairs. No other room options. I had reserved a room months in advance. The front desk lady said a few stairs, which I found odd being that there is an elevator. Beware…the top floor is by stairs only! Front desk lady ..."

Reviewed on 9 June 2026

Hyatt Regency O'Hare Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$513 per night from 3 July to 4 July
NZ$513
3 July - 4 July
includes taxes & fees
8.4/10 Very Good! (2,332 reviews)
"Food was top notch"

Reviewed on 7 June 2026

Hilton Chicago O'Hare Airport
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.

Discover the most popular places to visit in Chicago

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.