Northwest Chicago All inclusive Vacations

Book a All inclusive Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 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

Top All inclusive vacation packages in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
₩879,150
per person
Nov 21 - Nov 26
found 11 hours ago
Roundtrip flight included
Sioux City (SUX) to Chicago (ORD)
8.2/10 Very Good! (2,992 reviews)
Not the worst, just did not enjoy my stay. We tried to call the front desk multiple times, nobody would answer (it was 1am, says staff is available until 4am online). We even went downstairs and no one was available to help us. The shower had a hair in it, just not ideal assuming it would be cleaned before check in.

Reviewed on Sep 5, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
₩1,049,147
per person
Nov 21 - Nov 26
found 11 hours ago
Roundtrip flight included
Sioux City (SUX) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
The hotel was so amazing for us. Staff was accommodating and helped us immensely. The restaurant for breakfast and the roof top wil keep you coming back. We will try to stay there as much as we can while in Chicago.. Lester and Luis at the restaurants need a bonus. They kept the breakfast crowd well organized.

Reviewed on Sep 4, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
₩1,020,635
per person
Nov 21 - Nov 26
found 11 hours ago
Roundtrip flight included
Sioux City (SUX) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Cute hotel in great location..make sure to ask for a street side room or your view will be a brick wall and the room will be like a dark cave. 😭

Reviewed on Sep 4, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
₩1,162,038
per person
Nov 21 - Nov 26
found 11 hours ago
Roundtrip flight included
Sioux City (SUX) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
Beautiful hotel and fantastic staff.

Reviewed on Sep 4, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
₩1,113,548
per person
Nov 21 - Nov 26
found 11 hours ago
Roundtrip flight included
Sioux City (SUX) to Chicago (ORD)
8.8/10 Excellent! (2,341 reviews)
Don't see what you're looking for?
See all available trips from Sioux City to Northwest Chicago
View all trips
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.