Downtown Chicago Vacation Packages
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The Latest Downtown Chicago Vacation Packages
- Hotel Saint Clair- Magnificent Mile
Jan 21 - Jan 24Hotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property8.6/10 - Excellent (2,412 reviews)"great location and very clean and spacious room."Reviewed November 12, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • 1 stop ORD - YYZ • 1 stopCA $892CA $687found 1 day agoper traveller - The Peninsula Chicago
Jan 21 - Jan 24The Peninsula Chicago + Flight
Downtown Chicago3 nights5.0 star property9.8/10 - Exceptional (1,012 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • 1 stop ORD - YYZ • NonstopCA $1,944CA $1,379found 1 day agoper traveller - Sheraton Grand Chicago Riverwalk
Jan 21 - Jan 24Sheraton Grand Chicago Riverwalk + Flight
Downtown Chicago3 nights4.0 star property8.6/10 - Excellent (1,881 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • 1 stop ORD - YYZ • 1 stopCA $1,108CA $795found 1 day agoper traveller - Park Hyatt Chicago
Dec 29 - Jan 3Park Hyatt Chicago + Flight
Downtown Chicago5 nights5.0 star property9.6/10 - Exceptional (1,000 reviews)"This place was amazing and the hotel staff was extremely helpful"Reviewed November 10, 2026Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • 1 stop ORD - YUL • NonstopCA $3,257CA $2,340found 1 day agoper traveller - Le Méridien Essex Chicago
Jan 21 - Jan 24Le Méridien Essex Chicago + Flight
Downtown Chicago3 nights4.0 star property9.0/10 - Wonderful (1,000 reviews)"I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything."Reviewed November 3, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • 1 stop ORD - YYZ • 1 stopCA $952CA $710found 1 day agoper traveller
Where to stay in Downtown Chicago
Magnificent Mile
The Loop
River North
Lincoln Park
West Loop
Discover the most popular places to visit in Downtown Chicago
What to do near Downtown Chicago
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour
Downtown Chicago Hotel Deals
Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake Chicago
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile"Everything about the stay was amazing from beginning to end . The restaurant inside was also pretty tasty and the staff was exceptional."
Hampton Inn & Suites Chicago Downtown
Hampton Inn & Suites Chicago Downtown"Breakfaste are very well!"
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton"Everything was perfect"
"Very good"
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites"The hotel was basically clean, with no funky smells, and the location was fabulous. The layout of the room was also great, giving us some privacy, and we loved the view of Lake Michigan. However, the room was tired and definitely needed an update. The plugs and USB ports on one side of the bed didn't work, as did one of the house phones. Also, the door stopper in the bathroom was completely rusted, and dirty looking. The bed, in terms of comfort was also meh. Decent, but the sheets...
Hotel Saint Clair- Magnificent Mile
Hotel Saint Clair- Magnificent Mile"great location and very clean and spacious room."
La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago Downtown"Comfortable bed and pillows. Good breakfast. Friendly staff. Nice nearby parking."
Find out more about Downtown Chicago
Things to do in and around Downtown Chicago
Downtown Chicago is perfect for families seeking outdoor and city-themed adventures. Visitors can enjoy a vibrant shopping area, exciting arena entertainment, and a variety of theatres. With its bustling atmosphere and numerous attractions, this urban hub promises a memorable vacation filled with diverse activities for everyone.
Shopping
In Downtown Chicago, visit the 900 North Michigan Shops for a blend of entertainment and family-friendly vibes. The Shops at North Bridge offers a lively shopping scene, while Chicago Place Mall features diverse business and family options. Enjoy a vibrant shopping experience in this bustling city.
Recreation
Experience the vibrant sports atmosphere at the United Center, just 4.8km from Downtown Chicago. Immerse yourself in culture and entertainment at the Chicago Theatre, perfect for a romantic night out. Enjoy live music and great vibes at the House of Blues Chicago, a must-visit for any music lover.
Adventure
Amazing Chicago's Funhouse Maze offers a thrilling arcade experience with a whimsical twist, perfect for families seeking adventure. The Centennial Wheel provides stunning views of the city skyline while you enjoy the exhilarating ride. For a scenic hike, explore the Salt Creek Trail, where nature and outdoor beauty await.
Nightlife
Experience the vibrant nightlife in Downtown Chicago at Dave & Buster's, where you can enjoy drinks and entertainment in a lively atmosphere. For a romantic night, visit Kingston Mines or Blues on Halstead, both offering superb city vibes and captivating live music just a short drive away.
Find the best attractions in Downtown Chicago
Downtown Chicago is an ideal destination for families and outdoor enthusiasts, featuring iconic skyscrapers, urban parks, and historic buildings. Visitors can immerse themselves in the vibrant city life while exploring top attractions along the Chicago River. This bustling area caters to those seeking cultural experiences and family-friendly activities, making it a perfect spot for a memorable vacation in the heart of the Windy City.
- Navy Pier: Experience the vibrant atmosphere at Navy Pier, where you can enjoy stunning waterfront views, a variety of restaurants, and unique shops. This lively location offers entertainment options like the Ferris wheel and seasonal festivals, making it a perfect spot for families and friends alike.
- Michigan Avenue: Known as the Magnificent Mile, Michigan Avenue is a bustling street lined with upscale shops, iconic landmarks, and vibrant city energy. Explore its architecture and enjoy the dynamic blend of retail and dining experiences that capture the essence of Chicago.
- Millennium Park: A green oasis in the heart of the city, Millennium Park invites visitors to relax and enjoy outdoor art installations, beautiful gardens, and family-friendly events. Don't miss the famous Cloud Gate sculpture, affectionately known as The Bean, for a memorable photo opportunity.
Best time to go to Downtown Chicago
The best time to visit Downtown 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.
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 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.
Frequently Asked Questions
How much does a Downtown Chicago vacation package cost?
Go from looking to booking with our Downtown Chicago vacation packages, which start from just CA $687. Handpick the hotels and flights that suit your travel style. Then, add on a couple of tours or activities for an amazing adventure.
How do I get a cheap travel package to Downtown Chicago?
Bundle your bookings with Expedia to save big on your next trip. With more than 550 partner airlines and 1,000,000 hotels across the world, your Downtown Chicago vacation package can be tailored exactly to suit your budget. With all that extra money, why not include one or two fun tours and activities? It's an easy way to unlock even more savings. The vacation you've always dreamed of in Downtown Chicago is much closer than you thought!
How far in advance should I book my Downtown Chicago vacation?
While not all airlines advertise tickets early, you can normally look up international airfares on Expedia up to 12 months in advance. This is the time you'll score some incredible deals. If you've left things to the last minute, you could still be in luck. Discounted prices occasionally emerge a few weeks before departure.
What does an Expedia Downtown Chicago travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your ideal Downtown Chicago trip. You can also add on fun things like activities and tours once you've made your booking. You're in charge! When you combine your bookings with Expedia, you'll score discounts you won't find elsewhere.
What should I know before booking a Downtown Chicago travel package?
Our prices are always low. However, you'll pick up even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and tons of choice.
Can I choose my airline with a Downtown Chicago Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You're in charge! We have more than 550 partner airlines throughout the world, so you have lots of choice when arranging your Downtown Chicago trip.
If I'm not able to travel, can I cancel my Downtown Chicago vacation package?
You can. We understand that even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Downtown Chicago vacation package. You may be able to change or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.