Cheap Holidays to Chicago

Choose two or more items and save on your trip:

Top deals for trips to Chicago

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
4.5-star property

theWit Chicago, a Hilton Hotel

Downtown Chicago

25 Dec - 30 Dec

5 night stay

Zürich (ZRH) to Chicago (ORD)

Lufthansa • Direct return • Coach
Price was CHF 880, price is now CHF 619 per person
CHF 619
per person
just found
Our customers tell us that they can't get enough of the helpful staff at theWit Chicago, a Hilton Hotel. During your stay, you're just a quick walk from Michigan Avenue. Features include 2 bars, a full-service spa and a restaurant.
The Emily Hotel
4.0-star property

The Emily Hotel

Downtown Chicago

25 Dec - 30 Dec

5 night stay

Zürich (ZRH) to Chicago (ORD)

Lufthansa • Direct return • Coach
Price was CHF 1'152, price is now CHF 782 per person
CHF 782
per person
just found
Our customers tell us that they can't get enough of the helpful staff at The Emily Hotel. During your stay, you're just a quick walk from Milwaukee Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym.
Pendry Chicago
4.5-star property

Pendry Chicago

Downtown Chicago

25 Dec - 30 Dec

5 night stay

Zürich (ZRH) to Chicago (ORD)

Lufthansa • Direct return • Coach
Price was CHF 1'054, price is now CHF 731 per person
CHF 731
per person
just found
Our customers tell us they can't get enough of Pendry Chicago's great location. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym. This property offers pet-friendly amenities, such as food and water bowls.
Chicago Athletic Association, a Hyatt Hotel
4.5-star property

Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

25 Dec - 30 Dec

5 night stay

Zürich (ZRH) to Chicago (ORD)

Lufthansa • Direct return • Coach
Price was CHF 985, price is now CHF 695 per person
CHF 695
per person
just found
Our customers tell us that they can't get enough of the helpful staff at Chicago Athletic Association, a Hyatt Hotel. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 2 restaurants and 3 bars. This property offers pet-friendly amenities, such as food and water bowls.
Arlo Chicago
4.0-star property

Arlo Chicago

Downtown Chicago

25 Dec - 30 Dec

5 night stay

Zürich (ZRH) to Chicago (ORD)

Lufthansa • Direct return • Coach
Price was CHF 993, price is now CHF 720 per person
CHF 720
per person
just found
The sightseeing around Arlo Chicago gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a restaurant and a gym.

Chicago Holiday Packages for 5 Nights

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
4.5-star property

theWit Chicago, a Hilton Hotel

Downtown Chicago

25 Dec - 30 Dec

5 night stay

Zürich (ZRH) to Chicago (ORD)

Lufthansa • Direct return • Coach
Price was CHF 880, price is now CHF 619 per person
CHF 619
per person
just found
Our customers tell us that they can't get enough of the helpful staff at theWit Chicago, a Hilton Hotel. During your stay, you're just a quick walk from Michigan Avenue. Features include 2 bars, a full-service spa and a restaurant.
The Emily Hotel
4.0-star property

The Emily Hotel

Downtown Chicago

25 Dec - 30 Dec

5 night stay

Zürich (ZRH) to Chicago (ORD)

Lufthansa • Direct return • Coach
Price was CHF 1'152, price is now CHF 782 per person
CHF 782
per person
just found
Our customers tell us that they can't get enough of the helpful staff at The Emily Hotel. During your stay, you're just a quick walk from Milwaukee Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym.
Pendry Chicago
4.5-star property

Pendry Chicago

Downtown Chicago

25 Dec - 30 Dec

5 night stay

Zürich (ZRH) to Chicago (ORD)

Lufthansa • Direct return • Coach
Price was CHF 1'054, price is now CHF 731 per person
CHF 731
per person
just found
Our customers tell us they can't get enough of Pendry Chicago's great location. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym. This property offers pet-friendly amenities, such as food and water bowls.
Chicago Athletic Association, a Hyatt Hotel
4.5-star property

Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

25 Dec - 30 Dec

5 night stay

Zürich (ZRH) to Chicago (ORD)

Lufthansa • Direct return • Coach
Price was CHF 985, price is now CHF 695 per person
CHF 695
per person
just found
Our customers tell us that they can't get enough of the helpful staff at Chicago Athletic Association, a Hyatt Hotel. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 2 restaurants and 3 bars. This property offers pet-friendly amenities, such as food and water bowls.
Arlo Chicago
4.0-star property

Arlo Chicago

Downtown Chicago

25 Dec - 30 Dec

5 night stay

Zürich (ZRH) to Chicago (ORD)

Lufthansa • Direct return • Coach
Price was CHF 993, price is now CHF 720 per person
CHF 720
per person
just found
The sightseeing around Arlo Chicago gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a restaurant and a gym.

Cheap flights to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Chicago neighborhoods

Other holiday destinations

^Savings based on all package bookings with Flight + Hotel made on ebookers.ch from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.