Downtown Chicago Vacations from SAR1,628

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The Latest Downtown Chicago Vacation Packages

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

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 19 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (1,665 reviews)
Arlo Chicago is in the perfect location for walkable access to so many Chicago sights, excellent food (please try the Broken English Taco Pub around the corner!), bars, shopping, etc. It was also very conveniently located to access the L when we needed to get to other parts of the city! The staff was BEYOND accommodating, friendly, and helpful. The room was clean and exceeded all comfort expectations! I also highly recommend the lobby bar for a great happy hour spot!!! Everyone at this hotel was exceptional and I still cannot get over how wonderful the lobby smelled! Can't recommend Arlo Chicago enough!

Reviewed on 24 April 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 19 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (1,320 reviews)
A great hotel to have as a base to explore Chicago during day and in the evening. Room was great - comfortable, great shower. Short walk to train station to and from O'Hare airport.

Reviewed on 21 April 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 19 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
Front desk was very friendly and helpful. We had a corner unit and the view was great. The unit was very comfortable and clean.

Reviewed on 22 April 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
Jul 19 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Overall great experience. No complaints!!!

Reviewed on 22 April 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
Jul 19 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
8/10 Very Good! (1,524 reviews)
The only thing that we didn’t like was the fact that we got a parking ticket in front of the valet sign when we was told that it was saved to park there by the valet attendant

Reviewed on 24 April 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 SAR 561 per night from Apr 30 to May 1
SAR 561
SAR 658 total
includes taxes & fees
30 Apr - 1 May
8.2/10 Very Good! (3,927 reviews)
"Overall we enjoyed the stay and the property location is close to many restaurants, shops and subway. The complimentary breakfast was great."

Reviewed on 23 April 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 SAR 638 per night from May 3 to May 4
SAR 638
SAR 749 total
includes taxes & fees
3 May - 4 May
7.8/10 Good! (8,708 reviews)
"Awesome"

Reviewed on 24 April 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 SAR 603 per night from Apr 30 to May 1
SAR 603
SAR 707 total
includes taxes & fees
30 Apr - 1 May
8.8/10 Excellent! (2,153 reviews)
"Fitness Center and pool were closed. Housekeeping kept missing our room."

Reviewed on 25 April 2025

Hilton Chicago/Magnificent Mile Suites
See all 1,572 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.

Discover the most popular places to visit in Downtown Chicago

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

Michigan Avenue

4.5/5(332 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 featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its fascinating museums.

Navy Pier
Grant Park showing a garden and night scenes

Grant Park

4.5/5(3,318 reviews)

Grant Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its entertainment choices.

Grant Park