
Cheap Holidays to Chicago
- Top deals for trips to Chicago
- 3-night holiday deals
- 4-night holiday deals
- 5-night holiday deals
- 6 or 7-night holiday deals
Top deals for trips to Chicago
Price found within the past 48 hours. Click for updated prices.

4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 1'154, price is now CHF 729 per person
CHF 729
per person
found 2 days ago
During your stay at Hotel Riu Plaza Chicago, you're just a quick walk from Michigan Avenue. Enjoy features like free breakfast and free WiFi in public areas, plus 2 bars.

5.0-star property
Waldorf Astoria Chicago
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 2'118, price is now CHF 1'315 per person
CHF 1'315
per person
found 23 hours ago
Our customers tell us that they can't get enough of the helpful staff at Waldorf Astoria Chicago. During your stay, you'll be connected to a shopping centre and just a quick walk from Michigan Avenue. You'll find features such as free WiFi in public areas and a free area shuttle, plus a full-service spa. This property offers pet-friendly amenities, such as food and water bowls.

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 1'865, price is now CHF 1'168 per person
CHF 1'168
per person
found 1 day ago
Trump International Hotel & Tower Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. Free WiFi in public areas, a full-service spa and an indoor pool are available. This property offers pet-friendly amenities, such as food and water bowls.

5.0-star property
The Peninsula Chicago
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 2'130, price is now CHF 1'354 per person
CHF 1'354
per person
found 23 hours ago
The Peninsula Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 2 restaurants and a full-service spa. This property offers pet-friendly amenities, such as food and water bowls.

4.0-star property
Level Chicago – Old Town
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 1'250, price is now CHF 830 per person
CHF 830
per person
found 2 days ago
Level Chicago – Old Town's great location gets high marks from our customers. During your stay, you're just a quick walk from State Street. Enjoy features like free WiFi in public areas, plus a 24-hour gym and a coffee shop/cafe. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.
Chicago Holiday Packages for 6-7 Nights
Price found within the past 48 hours. Click for updated prices.

4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 1'154, price is now CHF 729 per person
CHF 729
per person
found 2 days ago
During your stay at Hotel Riu Plaza Chicago, you're just a quick walk from Michigan Avenue. Enjoy features like free breakfast and free WiFi in public areas, plus 2 bars.

5.0-star property
Waldorf Astoria Chicago
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 2'118, price is now CHF 1'315 per person
CHF 1'315
per person
found 23 hours ago
Our customers tell us that they can't get enough of the helpful staff at Waldorf Astoria Chicago. During your stay, you'll be connected to a shopping centre and just a quick walk from Michigan Avenue. You'll find features such as free WiFi in public areas and a free area shuttle, plus a full-service spa. This property offers pet-friendly amenities, such as food and water bowls.

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 1'865, price is now CHF 1'168 per person
CHF 1'168
per person
found 1 day ago
Trump International Hotel & Tower Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. Free WiFi in public areas, a full-service spa and an indoor pool are available. This property offers pet-friendly amenities, such as food and water bowls.

5.0-star property
The Peninsula Chicago
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 2'130, price is now CHF 1'354 per person
CHF 1'354
per person
found 23 hours ago
The Peninsula Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 2 restaurants and a full-service spa. This property offers pet-friendly amenities, such as food and water bowls.

4.0-star property
Level Chicago – Old Town
Downtown Chicago
25 Mar - 31 Mar
6 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct return • Coach
Price was CHF 1'250, price is now CHF 830 per person
CHF 830
per person
found 2 days ago
Level Chicago – Old Town's great location gets high marks from our customers. During your stay, you're just a quick walk from State Street. Enjoy features like free WiFi in public areas, plus a 24-hour gym and a coffee shop/cafe. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.
Best Chicago hotel deals for your holiday

Hilton Chicago
720 S Michigan Ave Chicago IL
The price is CHF 147 per night
CHF 147
1 Feb - 2 Feb
includes taxes & fees
0.96 km from city centre
Our customers tell us they can't get enough of Hilton Chicago's great location. During your stay, you're just a quick walk from State Street. Features include free WiFi in public areas, plus 2 restaurants and an indoor pool.
Pool
Whirlpool

Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
The price is CHF 154 per night
CHF 154
15 Feb - 16 Feb
includes taxes & fees
0.09 km from city centre
Our customers tell us they can't get enough of Palmer House a Hilton Hotel's great location. During your stay, you're just a quick walk from Millennium Park. You'll find features such as a full-service spa, an indoor pool and a restaurant.
Pool
Wellness

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
The price is CHF 75 per night
CHF 75
15 Feb - 16 Feb
includes taxes & fees
2.17 km from city centre
The shopping around Hilton Chicago/Magnificent Mile Suites gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as free WiFi in public areas, plus an indoor pool and a gym.
Pool
Haustierfreundlich

Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
The price is CHF 77 per night
CHF 77
29 Jan - 30 Jan
includes taxes & fees
0.8 km from city centre
Our customers tell us that they can't get enough of the helpful staff at Club Quarters Hotel Wacker at Michigan, Chicago. During your stay, you're just a quick walk from Chicago Riverwalk. You'll find features such as free WiFi in public areas, plus a restaurant and a gym. This property offers pet-friendly amenities, such as food and water bowls.
Haustierfreundlich
Kostenloses WLAN

Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
The price is CHF 185 per night
CHF 185
6 Feb - 7 Feb
includes taxes & fees
25.73 km from city centre
Our customers tell us that they can't get enough of the helpful staff at Hilton Chicago O'Hare Airport. During your stay, you'll be connected to the airport and close to Allstate Arena. Free WiFi in public areas, a free round-trip airport shuttle and 2 restaurants are available.
Kostenloser Flughafentransfer
Haustierfreundlich

Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
The price is CHF 101 per night
CHF 101
19 Jan - 20 Jan
includes taxes & fees
1.33 km from city centre
The free breakfast at Embassy Suites by Hilton Chicago Downtown River North gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as a free manager's reception, plus an indoor pool and a restaurant.
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.
Cheap flights to Chicago
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
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^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.
