Downtown Chicago Vacations from AED2,500
Book a Hotel + Flight together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to AED 148 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Downtown Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (2,269 reviews)
Beautiful space, right near the lake. Also has a cozy little restaurant on the 1st floor
Reviewed on 3 June 2025
Chicago River Side Suites
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,598 reviews)
This is the second time that we have stayed at the Trump hotel. It’s a beautiful property in a prime location. There are amazing views of the river and lake. The hotel is within walking distance of shopping, restaurants, and other fun sites! The spa is provides great service! I will definitely stay there again!
Reviewed on 1 June 2025
The Royal Sonesta Chicago River North
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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 The carpets were stained and worn down, and the sheets and rooms were very old and outdated.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
Palmer House a Hilton Hotel
Downtown Chicago
per person
Aug 7 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
8.4/10 Very Good! (1,733 reviews)
Location was great, walkable to anywhere in downtown Chicago, Millennium Park, Soldier Field, etc.
Reviewed on 27 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
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.
Downtown Chicago Hotel Deals
Congress Plaza Hotel
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! (8,826 reviews)
"The facility has a great location in walking distance to many attractions. The family suite had a small bathroom with limited space."
Reviewed on 3 June 2025
citizenM Chicago Downtown
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! (3,134 reviews)
"Nice clean hotel. Close to it all downtown"
Reviewed on 2 June 2025
The Westin Michigan Avenue Chicago
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! (1,009 reviews)
"Absolutely top tier!! Definitely a whole vibe."
Reviewed on 30 May 2025
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
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.
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.
Millennium Park
4.5/5(7,198 reviews)
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.