Why should I book my Downtown Chicago holiday with Expedia?

Expedia has your back for every detail of your next Downtown Chicago holiday. You'll always get the best deal possible, but when you bundle your flights, hotel and/or car hire into a holiday package, you'll save even more. Want to truly make the most of your escape? Add some awesome tours and activities to your package. We offer flexible cancellation policies on most bookings, so you won't need to worry if you have to change your plans. Head over to our Customer Service Portal link to find out more.

How do I get a cheap holiday to Downtown Chicago?

Secure flights that fit your busy schedule, add a hotel room to your booking and watch how much you save with a Downtown Chicago holiday. It's as simple as that! From hotels and flights to hire cars and tours, Expedia makes travelling cheaply a cinch. And with more than 400 air carriers and 321,000 hotel options globally to select from, you'll never be short of choice. Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.

What should I do on my Downtown Chicago holiday?

There are plenty of things to put on your travel itinerary during your holiday in Downtown Chicago. Millennium Park , Willis Tower , Art Institute of Chicago and John Hancock Centre are a few of the major attractions.

Do I need a visa for my Downtown Chicago holiday?

Research the latest information on official government websites. Your nationality and whether you're visiting for study, leisure or business will determine if you need a visa for Downtown Chicago. Familiarise yourself with the application process, including the required documentation, fees and turnaround times. Finalise your application well in advance to allow sufficient processing time. Some visas may take many weeks or even months to obtain, depending on the country and time of year.

What should I wear on my Downtown Chicago holiday?

Though everyone's style varies, it can help to have some guidelines for what to bring during your holiday in Downtown Chicago. Think about browsing style blogs before you head off for inspiration on local dress codes or fashion trends.

What does an Expedia Downtown Chicago holiday include?

Flights, hotels and hire cars — you'll find them all here. With Expedia, you can create your Downtown Chicago travel package however you want. All you have to do is decide exactly what you need. Once you've made your booking, why not add extras like activities and tours? The more you bundle, the greater the savings! Expedia has a wide selection of properties in Downtown Chicago, allowing you the freedom to personalise your holiday. Apartments and private holiday homes are two of the most sought-after stays for our customers here.

Does Expedia offer Book Now, Pay Later Downtown Chicago holidays?

We do. Expedia has joined forces with online lender Klarna to help you easily pay for your trip in instalments. Simply pick the payment plan that works for you during checkout and take the stress out of budgeting for your next trip. Make sure you bundle your flights, car hire and hotel with Expedia to get the biggest bang for your travel buck. Browse our flexible payment options below: Pay monthly holidays : Jet off on that dream holiday sooner with Klarna's manageable monthly instalment plans. If paying in multiple transactions sounds right for you, choose this option at checkout. No-deposit holidays : Pressing the "book now" button is easier with this payment plan. With no deposit required for your escape, you can Book Now, Pay Later and get on your way.

Can I choose my airline with a Downtown Chicago Expedia holiday?

Yes, and with more than 400 airlines to pick from globally, you're spoiled for choice. Have a look through the available options and see which airline suits your budget and needs.

Downtown Chicago Holidays 2026 from £1,469

Things to do in and around Downtown Chicago

Downtown Chicago is perfect for family outings and city-themed holidays, offering a vibrant mix of activities. Visitors can enjoy shopping in bustling districts, experience thrilling events at arena entertainment facilities, and catch a show in one of the many theatres. A noteworthy highlight is exploring the Holiday Inn, a convenient base to discover all that this exciting area has to offer.

Shopping

Experience the vibrant shopping scene in Downtown Chicago at the Shops at North Bridge, offering a mix of entertainment and family-friendly vibes. Alternatively, visit the Chicago Place Mall for a variety of shops. Don't miss the Maxwell Street Market, where you can find unique treasures and local goods.

Recreation

Experience the thrill of sporting events at Soldier Field, just 3.2km from Downtown Chicago, where the energy is palpable. Enjoy cultural performances at the historic Chicago Theatre, perfect for family outings. Immerse yourself in live music and vibrant atmosphere at the House of Blues Chicago for an unforgettable night.

Adventure

Experience the thrill at Amazing Chicago's Funhouse Maze, where family-friendly fun meets adventure. Take a ride on the Centennial Wheel for stunning city views. For outdoor enthusiasts, the Salt Creek Trail offers invigorating hiking amidst beautiful scenery, located 19.3km from Downtown Chicago.

Nightlife

Experience the vibrant nightlife of Downtown Chicago at Dave & Buster's, where fun and romance blend seamlessly. For a lively atmosphere, head to Kingston Mines or Blues on Halstead, both offering captivating city vibes and entertainment just a short distance away.

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

Find the best attractions in Downtown Chicago

Downtown Chicago offers a delightful blend of family-friendly activities and urban exploration, featuring iconic skyscrapers, picturesque parks, and historic buildings. Visitors can immerse themselves in the local culture while exploring top attractions, including renowned museums and the scenic Chicago River. Whether you're seeking a vibrant city experience or leisurely outdoor pursuits, Downtown Chicago presents a variety of exciting options for every traveller.

Navy Pier: Experience the vibrant atmosphere of Navy Pier, a bustling jetty that offers stunning views of Lake Michigan. Enjoy a variety of attractions, from amusement rides to restaurants, all while soaking in the friendly, urban vibe that makes this location a favourite among locals and tourists alike.
Michigan Avenue: Stroll down Michigan Avenue, a renowned street famous for its shopping and dining options. The lively city vibes create an exciting backdrop as you explore iconic architecture, visit upscale boutiques, and enjoy the vibrant energy of downtown Chicago.
Millennium Park: Discover Millennium Park, an urban oasis that combines art, nature, and community. With its family-friendly atmosphere, outdoor concerts, and stunning public art installations like the Cloud Gate, this park is perfect for a leisurely day out in the city.

Best time to go to Downtown Chicago

The best time to visit Downtown Chicago can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Downtown Chicago falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature around Downtown Chicago falls in January, visitor numbers are slightly low and weather is mostly with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly	Slightly Low	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly	Slightly Low	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly	Average	Average
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Average	Average
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Average	Average
December	33.1°F (0.6°C)	Light Rain	Mostly	Average	Slightly Low

Tips to save on your trip to Downtown 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 Downtown 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.

Where to stay in Downtown Chicago

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

Top hotels in Downtown Chicago

Hotel Felix River North/Magnificent Mile

111 W Huron St Chicago IL

Fully refundableReserve now, pay when you stay

£98

25 May - 26 May

includes taxes & fees

8.2/10 Very Good! (2,656 reviews)

I never made it to hotel due to airline canceling flight. The hotel would not give me full refund for something that was out of my control. I WOULD NEVER BOOK WITH THIS HOTEL AGAIN. there should be courtesy given when your flight is canceled and you have no way to get there.

Reviewed on 1 May 2026

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

£118

26 May - 27 May

includes taxes & fees

8.8/10 Excellent! (5,147 reviews)

Room was a little small but worked out perfect! Great location.

Reviewed on 2 May 2026

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street Chicago IL

Fully refundableReserve now, pay when you stay

£96

25 May - 26 May

includes taxes & fees

8.8/10 Excellent! (3,472 reviews)

I had a very disappointing experience at this hotel. The room was very old and had a strong unpleasant smell as soon as we entered. The bed was also too short and uncomfortable, making it impossible to rest properly. Because of these issues, we decided to leave after only one hour and could not continue ...

Reviewed on 1 May 2026

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.