Downtown Chicago Vacation Packages

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Top Holiday Package Deals in Downtown Chicago

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 4 - Jul. 7
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Gorgeous views, great in room dining, staff were very nice

Reviewed on Apr. 28, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
TV did not work. Was told that it was a problem with the system for everyone and would be fixed in 10 minutes. An hour later I called again and was told the engineer would come to our room next. The engineer never came. No follow up from anyone else. The TV did not work until the next day.

Reviewed on Apr. 29, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,665 reviews)
Good room, comfortable bed, excellent location.

Reviewed on Apr. 26, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (1,046 reviews)
I stay here everytime I visit home. Great space and location.

Reviewed on Apr. 29, 2025

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Great property in Chicago. Quiet rooms

Reviewed on Apr. 28, 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

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Find hotels in Magnificent Mile

Downtown Chicago Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $242 per night from May 1 to May 2
CA $242
CA $284 total
includes taxes & fees
May 1 - May 2
8.2/10 Very Good! (3,960 reviews)
"Very smooth check in, we had a great stay. Very helpful at the front not only at check in but with directions and help throughout the stay."

Reviewed on Apr. 29, 2025

Embassy Suites by Hilton Chicago Downtown River North
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 CA $165 per night from May 28 to May 29
CA $165
CA $193 total
includes taxes & fees
May 28 - May 29
7.8/10 Good! (8,715 reviews)
"Really nice hotel next to millennium park."

Reviewed on Apr. 28, 2025

Congress Plaza Hotel
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 CA $222 per night from May 8 to May 9
CA $222
CA $261 total
includes taxes & fees
May 8 - May 9
8.8/10 Excellent! (2,164 reviews)
"Pool and fitness center was not in service."

Reviewed on Apr. 28, 2025

Hilton Chicago/Magnificent Mile Suites
See all 1,587 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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 $842. 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.

Discover the most popular places to visit in Downtown Chicago

Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy 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
Navy Pier

Navy Pier

4.5/5(459 reviews)

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

Navy Pier
Grant Park

Grant Park

4.5/5(291 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Things to do

Flyover in Chicago

Flyover in Chicago

CA $53
per adult
98% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

CA $67
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

CA $62
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
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.