Downtown Chicago Holidays from £1,480
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The Latest Downtown Chicago Holiday Packages
- Level Chicago - River North
9 Oct - 14 OctLevel Chicago - River North + Flight
Downtown Chicago5 nights4.0 star property9.2/10 - Wonderful (1,042 reviews)"This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities"Reviewed July 30, 2026Return • Edinburgh (EDI) - Chicago (ORD)EDI - ORD • 1 stop MDW - EDI • 2 stops£2,079£1,480found 18 hours agoper traveller - Sable at Navy Pier Chicago, Curio Collection by Hilton
9 Oct - 14 OctSable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago5 nights4.0 star property9.4/10 - Exceptional (2,622 reviews)Return • Edinburgh (EDI) - Chicago (ORD)EDI - ORD • 1 stop MDW - EDI • 2 stops - Eurostars Magnificent Mile
9 Oct - 14 OctEurostars Magnificent Mile + Flight
Downtown Chicago5 nights4.0 star property9.0/10 - Wonderful (3,760 reviews)"Room was clean…Welcoming staff..Perfect a/c cuz it was Heat waive when we visited Chicago…Parking was awesome cuz we just valeted our car!"Reviewed July 30, 2026Return • Edinburgh (EDI) - Chicago (ORD)EDI - ORD • 1 stop MDW - EDI • 2 stops - Four Seasons Hotel Chicago
9 Oct - 14 OctFour Seasons Hotel Chicago + Flight
Downtown Chicago5 nights5.0 star property9.4/10 - Exceptional (1,000 reviews)Return • Edinburgh (EDI) - Chicago (ORD)EDI - ORD • 1 stop MDW - EDI • 2 stops - Sports Illustrated Resorts Chicago
9 Oct - 14 OctSports Illustrated Resorts Chicago + Flight
Downtown Chicago5 nights3.5 star property9.0/10 - Wonderful (1,438 reviews)"I will never stay at this hotel again. The staff and policies are a joke. Could not recommend them less."Reviewed July 30, 2026Return • Edinburgh (EDI) - Chicago (ORD)EDI - ORD • 1 stop MDW - EDI • 2 stops
Discover the most popular places to visit in Downtown Chicago
What to do near Downtown Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Ticket
Downtown Chicago Hotel Deals
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton
Holiday Inn Chicago Dwtn - The Mart by IHG
Holiday Inn Chicago Dwtn - The Mart by IHG
Claridge House Chicago, Tapestry Collection by Hilton
Claridge House Chicago, Tapestry Collection by HiltonFrequently Asked Questions
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.
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Things to do in and around Downtown Chicago
Downtown Chicago is perfect for family outings and outdoor adventures, featuring vibrant shopping areas, an exciting arena for entertainment, and a variety of theatres. Visitors can also explore the nearby Holiday Inn, making it an ideal base for discovering the city's attractions. With its rich urban atmosphere, Downtown Chicago promises a memorable experience for all types of vacationers.
Shopping
The Shops at North Bridge offers a vibrant shopping experience with a blend of entertainment and family-friendly options. Nearby, Chicago Place Mall provides a bustling atmosphere perfect for business and family vibes. For unique finds, visit Maxwell Street Market, where the local culture thrives amidst a lively city backdrop.
Recreation
Experience the vibrant sports atmosphere at the United Center, just 4.8km away, where you can catch a thrilling game. In Downtown Chicago, enjoy the artistic charm of the Chicago Theatre, perfect for a romantic evening or family outing, followed by live music at Lincoln Hall, also 4.8km away.
Adventure
Experience the thrill of Amazing Chicago's Funhouse Maze, where family adventures await in a vibrant arcade. Take a ride on the iconic Centennial Wheel for stunning views, or explore the scenic Salt Creek Trail, a 19.3km hiking path perfect for outdoor enthusiasts seeking adventure.
Nightlife
For a vibrant nightlife experience in Downtown Chicago, visit Dave & Buster's for a lively pub atmosphere. Just a short distance away, Kingston Mines and Blues on Halstead offer fantastic nightclubs with romance and city vibes, perfect for enjoying live music and dancing the night away.
Find the best attractions in Downtown Chicago
Downtown Chicago offers a delightful experience for families and city enthusiasts alike, featuring iconic skyscrapers, urban parks, and historic buildings. Visitors can explore cultural attractions, enjoy the scenic Chicago River, and visit renowned museums. With a plethora of top attractions, Downtown Chicago is an ideal destination for those seeking a vibrant city atmosphere infused with rich history and family-friendly activities.
- Navy Pier: Experience the vibrant atmosphere of Navy Pier, a bustling hub featuring stunning waterfront views, dining, and entertainment options. Enjoy the scenic surroundings and friendly locals while taking in the sights from the Ferris wheel or relaxing by the lake.
- Michigan Avenue: Stroll along the iconic Michigan Avenue, known as the Magnificent Mile. This bustling street offers a mix of high-end shops, restaurants, and cultural landmarks, providing a quintessential urban experience in the heart of Chicago.
- Millennium Park: Discover the beauty of Millennium Park, an urban oasis perfect for families. Enjoy outdoor concerts, art installations, and the famous Cloud Gate sculpture, all while soaking in the vibrant city atmosphere.
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 cloudy with light rain.
Tips to save on your trip to Downtown Chicago
- Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Downtown Chicago.
- Consider traveling to Downtown Chicago during the low season (December to February) for more affordable options.
- 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.