Downtown Chicago Holidays

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Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Sept - 10 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
Hotel was great for the price. Close to Michigan and there’s plenty of food options that are walking distance. Rooms are ok, they could use a fridge and microwave for those who like to reheat their food or store any groceries they may buy if staying for a few days. (This is a preference). Overall, I enjoyed my stay.

Reviewed on 19 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Sept - 10 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
The property was very clean and well-maintained, offering an amazing view that made our stay truly memorable. Highly recommend for anyone looking for a relaxing and scenic getaway

Reviewed on 18 Jul 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Sept - 10 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
We were happy with every aspect of our stay!

Reviewed on 19 Jul 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Sept - 10 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
Staff was super helpful.

Reviewed on 17 Jul 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Sept - 10 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Amazing place overall

Reviewed on 15 Jul 2025

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
Magnificent Mile - River North

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

Find hotels in Magnificent Mile

Top hotels in Downtown Chicago

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 €179 per night from 4 Aug to 5 Aug
€179
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,985 reviews)
"Historic hotel!"

Reviewed on 16 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is €299 per night from 19 Aug to 20 Aug
€299
19 Aug - 20 Aug
includes taxes & fees
9/10 Wonderful! (2,063 reviews)
"Convenient"

Reviewed on 17 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €148 per night from 10 Aug to 11 Aug
€148
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (2,474 reviews)
"Rocky was awesome and gave us great recommendations. Check in lady was nice and had no issues. Only issue we had was the bar. My husband waiting a good 30 min with no acknowledgment and it wasn’t busy. This happened 2 nights in a row. Someone from the food area noticed he hadn’t been helped and helped ..."

Reviewed on 18 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 1,670 properties in Downtown Chicago
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.

Frequently asked questions

How much does a Downtown Chicago holiday package cost?
Go from looking to booking with our Downtown Chicago holiday packages, which start from just €643. 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 holiday 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 holiday you've always dreamed of in Downtown Chicago is much closer than you thought!
How far in advance should I book my Downtown Chicago holiday?
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 holiday package?
Yes — that's the beauty of an Expedia holiday 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 holiday 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 holiday 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.

Popular places to visit

Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Millennium Park featuring street scenes, autumn leaves and modern architecture

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

Things to do

River tour boat in Chicago

Architecture River Tour

€41
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€38
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€38
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.