Old Town Chicago Vacations from AED6,444

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to AED 148 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

The Latest Old Town Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Chicago (ORD)
8.4/10 Very Good! (3,744 reviews)
The hotel is very nice. The breakfast was quite basic, but it's great that they offer it.

Reviewed on 19 May 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
Great property with friendly and helpful staff

Reviewed on 18 May 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
Amazing views and comfortable rooms. Amenities were excellent.

Reviewed on 20 May 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Chicago (ORD)
9.2/10 Wonderful! (1,665 reviews)
I took my mom there for Mother’s Day weekend & she loved it! It was convenient to EVERYTHING! We walked to the Bane, shopping(Macy, Loft) & restaurant all walking distance. The staffs were very friendly & helpful! Planning on coming back anytime I visit Chicago!

Reviewed on 20 May 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Chicago (ORD)
9/10 Wonderful! (1,046 reviews)
Loved this hotel. Very chic

Reviewed on 18 May 2025

Where to stay in Old Town Chicago

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

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Old Town Chicago Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is AED 420 per night from May 26 to May 27
AED 420
AED 494 total
includes taxes & fees
26 May - 27 May
7.8/10 Good! (8,887 reviews)
"Awesome!"

Reviewed on 20 May 2025

Congress Plaza Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
The price is AED 397 per night from May 26 to May 27
AED 397
AED 557 total
includes taxes & fees
26 May - 27 May
8/10 Very Good! (2,877 reviews)
"Great location. Room was decently sized and clean."

Reviewed on 19 May 2025

Warwick Allerton - Chicago
Ambassador Hotel Chicago
Ambassador Hotel Chicago
4 out of 5
1301 N State Pkwy, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 122 per night from May 21 to May 22
AED 122
AED 678 total
includes taxes & fees
21 May - 22 May
8.4/10 Very Good! (1,023 reviews)
"Beautiful hotel in a nice neighborhood of Chicago"

Reviewed on 15 May 2025

Ambassador Hotel Chicago
See all 4,179 properties in Old Town 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 Old Town Chicago

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Wrigley Field
Six Flags Great America featuring rides

Six Flags Great America

4.5/5(347 reviews)

Enjoy the excitement at Six Flags Great America and see why people love this theme park in Gurnee. Stroll along the lakeside or visit the shops in this family-friendly area.

Six Flags Great America
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