Downtown Chicago Vacations

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Your Downtown Chicago Vacation

Reserving a Downtown Chicago vacation package is an ideal way to get to know this neighborhood. From its well-known places to its little-known secrets, you won't be short of new adventures. Hoping to explore the sights during your trip to Downtown Chicago? Make sure you stop by nearby attractions like Millennium Park, Willis Tower and Art Institute of Chicago. Expedia will help put your travel plans into action. Book your dream Downtown Chicago vacation today.

The Latest Downtown Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.8/10 Excellent! (206 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on Mar 16, 2024

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
Jul 18 - Jul 22
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (3,494 reviews)
Location was fantastic and the property is beautiful!

Reviewed on May 15, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The best hotel hands down!

Reviewed on May 13, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (96 reviews)
Outstanding service and facility.

Reviewed on Jan 10, 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 22
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,005 reviews)
We have a plenty staying at this hotel has the best locations and restaurant is so good

Reviewed on May 13, 2024

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

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 $167 per night from May 27 to May 28
$167
$196 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (6,728 reviews)
"I really liked how clean the room was."

Reviewed on May 14, 2024

Congress Plaza Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $105 per night from May 29 to May 30
$105
$138 total
includes taxes & fees
May 29 - May 30
7.6/10 Good! (2,578 reviews)
"Very clean"

Reviewed on May 14, 2024

Warwick Allerton - Chicago
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $153 per night from May 27 to May 28
$153
$205 total
includes taxes & fees
May 27 - May 28
8.6/10 Excellent! (1,001 reviews)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"

Reviewed on May 10, 2024

The Westin Michigan Avenue Chicago
See all 1,636 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.

Explore other types of vacation packages

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All Inclusive Vacations

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Beach Vacations

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Kid Friendly 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 $678. 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

Image for Navy Pier

Navy Pier

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

Navy Pier
Image for Grant Park

Grant Park

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
Image for Millennium Park

Millennium Park

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

Millennium Park

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

$229
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

$54
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
See all activities in Chicago

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.