Downtown Chicago Vacations from AED5,171

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The Latest Downtown Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Chicago (ORD)
9.2/10 Wonderful! (1,754 reviews)
Our stay was ok. The hotel was not as updated as the pictures on the site shows. The carpets were stained and worn down, and the sheets and rooms were very old and outdated. The rooftop looked nothing like the photos. Otherwise it’s in a great location.

Reviewed on 31 May 2025

Chicago River Side Suites

Chicago River Side Suites

2 out of 5
Downtown Chicago
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Chicago (ORD)
No reviews
Perfect location. The roads are very clean and most importantly the mattress was very comfortable. We had the option to use a non pet friendly rooms since I have allergies and got a room higher floor for a free upgrade. So far one of the best hotels I’ve ever stayed at.

Reviewed on 24 May 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Chicago (ORD)
9/10 Wonderful! (315 reviews)
I had no idea how nice this property would be! I had a full one-bedroom apartment and amazing view and amenities. 10/10, would stay again!

Reviewed on 1 June 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Beautiful hotel and wonderful staff!

Reviewed on 21 May 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Chicago (ORD)
9.2/10 Wonderful! (1,093 reviews)
Beautiful and modern. Easy check in and checkout. Brunch and lunch in the restaurant were delicious and affordable.

Reviewed on 31 May 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

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 AED 526 per night from Jul 3 to Jul 4
AED 526
AED 617 total
includes taxes & fees
3 Jul - 4 Jul
7.8/10 Good! (8,790 reviews)
"Property could use renovations"

Reviewed on 31 May 2025

Congress Plaza Hotel
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 528 per night from Jul 1 to Jul 2
AED 528
AED 619 total
includes taxes & fees
1 Jul - 2 Jul
9.2/10 Wonderful! (3,126 reviews)
"Great staff"

Reviewed on 1 June 2025

citizenM Chicago Downtown
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 AED 525 per night from Jun 30 to Jul 1
AED 525
AED 727 total
includes taxes & fees
30 Jun - 1 Jul
8.8/10 Excellent! (1,006 reviews)
"Absolutely top tier!! Definitely a whole vibe."

Reviewed on 30 May 2025

The Westin Michigan Avenue Chicago
See all 1,658 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

Navy Pier featuring a sunset and rides

Navy Pier

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
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
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

After visiting Millennium Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

Millennium Park