Cragin Vacations from $225

Book a Hotel + Flight or Car together to unlock savings

Your Cragin Vacation

Discover all the amazing things this neighborhood has to offer with a tailor-made Cragin vacation package. However you picture yourself spending your days here, you'll find countless opportunities for fun, relaxation and adventure. When it's time to take in the sights, you'll find loads of big-name attractions nearby including Portage Park, Walt Disney House and Six Corners. Visit one, two or more during your trip to Cragin. Expedia will help put your travel plans into action. Book your dream Cragin vacation today.

The Latest Cragin Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $455, price is now $225 per person
$225
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine

Reviewed on Oct 4, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,560, price is now $624 per person
$624
per person
Dec 23 - Dec 28
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,046 reviews)
One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $981, price is now $514 per person
$514
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend

Reviewed on Oct 7, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $704, price is now $384 per person
$384
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast are fresh. Shops are near by.

Reviewed on Oct 10, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $999, price is now $556 per person
$556
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Perfect location and atmosphere

Reviewed on Oct 7, 2025

Where to stay in Cragin

Find the best Cragin areas and neighborhoods for the activities you enjoy most. Learn more about Cragin
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Cragin 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
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,331 reviews)
"Very clean"

Reviewed on Oct 7, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $107 total per night from Nov 10 to Nov 11
$107 total
Nov 10 - Nov 11
Total with taxes and fees
7.8/10 Good! (2,435 reviews)
"Great place"

Reviewed on Oct 8, 2025

Freehand Chicago
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
$165 nightly
The price is $193 total per night from Nov 9 to Nov 10
$193 total
Nov 9 - Nov 10
Total with taxes and fees
8.4/10 Very Good! (5,063 reviews)
"Great place, good breakfast and the location"

Reviewed on Oct 8, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,782 properties in Cragin
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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Cragin

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

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 featuring a sunset and rides

Navy Pier

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

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel 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.