
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
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
13 Oct - 19 Oct
6 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 1'521, price is now CHF 988 per person
CHF 988
per person
found 6 hours ago
The shopping around Sable at Navy Pier Chicago, Curio Collection by Hilton gets high marks from our customers. During your stay, you'll be connected to the convention centre and just a quick walk from Lake Michigan. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.

4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
13 Oct - 19 Oct
6 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 1'661, price is now CHF 999 per person
CHF 999
per person
found 7 hours ago
Our customers tell us they can't get enough of The Royal Sonesta Chicago River North's great location. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus an indoor pool and a restaurant. This property offers pet-friendly amenities, such as food and water bowls.

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
13 Oct - 19 Oct
6 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 2'430, price is now CHF 1'482 per person
CHF 1'482
per person
found 7 hours 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.

4.0-star property
Level Chicago – Old Town
Downtown Chicago
13 Oct - 19 Oct
6 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 1'693, price is now CHF 1'071 per person
CHF 1'071
per person
found 7 hours 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.

5.0-star property
Park Hyatt Chicago
Downtown Chicago
13 Oct - 19 Oct
6 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 2'623, price is now CHF 1'685 per person
CHF 1'685
per person
found 7 hours ago
Our customers tell us that they can't get enough of the helpful staff at Park Hyatt Chicago. During your stay, you'll be connected to a shopping centre and just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a full-service spa and an indoor pool. This property offers pet-friendly amenities, such as food and water bowls.
Chicago Holiday Packages for 5 Nights
Price found within the past 48 hours. Click for updated prices.

4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
13 Oct - 18 Oct
5 night stay
Zürich (ZRH) to Chicago (ORD)
LOT-Polish Airlines • Direct return • Coach
Price was CHF 1'486, price is now CHF 1'053 per person
CHF 1'053
per person
found 6 hours ago
The shopping around Sable at Navy Pier Chicago, Curio Collection by Hilton gets high marks from our customers. During your stay, you'll be connected to the convention centre and just a quick walk from Lake Michigan. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
13 Oct - 18 Oct
5 night stay
Zürich (ZRH) to Chicago (ORD)
LOT-Polish Airlines • Direct return • Coach
Price was CHF 2'252, price is now CHF 1'465 per person
CHF 1'465
per person
found 6 hours 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.

4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
13 Oct - 18 Oct
5 night stay
Zürich (ZRH) to Chicago (ORD)
LOT-Polish Airlines • Direct return • Coach
Price was CHF 1'622, price is now CHF 1'068 per person
CHF 1'068
per person
found 6 hours ago
Our customers tell us they can't get enough of The Royal Sonesta Chicago River North's great location. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus an indoor pool and a restaurant. This property offers pet-friendly amenities, such as food and water bowls.

5.0-star property
Park Hyatt Chicago
Downtown Chicago
13 Oct - 18 Oct
5 night stay
Zürich (ZRH) to Chicago (ORD)
LOT-Polish Airlines • Direct return • Coach
Price was CHF 2'419, price is now CHF 1'637 per person
CHF 1'637
per person
found 6 hours ago
Our customers tell us that they can't get enough of the helpful staff at Park Hyatt Chicago. During your stay, you'll be connected to a shopping centre and just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a full-service spa and an indoor pool. This property offers pet-friendly amenities, such as food and water bowls.

4.0-star property
Level Chicago – Old Town
Downtown Chicago
13 Oct - 18 Oct
5 night stay
Zürich (ZRH) to Chicago (ORD)
LOT-Polish Airlines • Direct return • Coach
Price was CHF 1'644, price is now CHF 1'125 per person
CHF 1'125
per person
found 6 hours 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
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
13 Oct - 19 Oct
6 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 1'521, price is now CHF 988 per person
CHF 988
per person
found 6 hours ago
The shopping around Sable at Navy Pier Chicago, Curio Collection by Hilton gets high marks from our customers. During your stay, you'll be connected to the convention centre and just a quick walk from Lake Michigan. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.

4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
13 Oct - 19 Oct
6 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 1'661, price is now CHF 999 per person
CHF 999
per person
found 7 hours ago
Our customers tell us they can't get enough of The Royal Sonesta Chicago River North's great location. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus an indoor pool and a restaurant. This property offers pet-friendly amenities, such as food and water bowls.

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
13 Oct - 19 Oct
6 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 2'430, price is now CHF 1'482 per person
CHF 1'482
per person
found 7 hours 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.

4.0-star property
Level Chicago – Old Town
Downtown Chicago
13 Oct - 19 Oct
6 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 1'693, price is now CHF 1'071 per person
CHF 1'071
per person
found 7 hours 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.

5.0-star property
Park Hyatt Chicago
Downtown Chicago
13 Oct - 19 Oct
6 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 2'623, price is now CHF 1'685 per person
CHF 1'685
per person
found 7 hours ago
Our customers tell us that they can't get enough of the helpful staff at Park Hyatt Chicago. During your stay, you'll be connected to a shopping centre and just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a full-service spa and an indoor pool. This property offers pet-friendly amenities, such as food and water bowls.
Best Chicago hotel deals for your holiday

The Wade
644 N Lake Shore Dr, Chicago, IL
The price is CHF 143 per night
CHF 143
1 Sept - 2 Sept
includes taxes & fees
1.8 km from city centre
Our customers tell us they can't get enough of The Wade's great location. During your stay, you're just a quick walk from Lake Michigan. Free WiFi in public areas, an indoor pool and a restaurant are available.
Pool
Haustierfreundlich

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
The price is CHF 186 per night
CHF 186
15 Sept - 16 Sept
includes taxes & fees
0.69 km from city centre
Our customers tell us they can't get enough of Congress Plaza Hotel's great location. During your stay, you're just a quick walk from Millennium Park. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
Kostenloses WLAN
Restaurant

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is CHF 144 per night
CHF 144
3 Sept - 4 Sept
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.
Pool
Frühstück inbegriffen

Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
The price is CHF 184 per night
CHF 184
2 Sept - 3 Sept
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 Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
The price is CHF 135 per night
CHF 135
2 Sept - 3 Sept
includes taxes & fees
1.21 km from city centre
Our customers tell us that they can't get enough of the sightseeing around Hilton Garden Inn Chicago Downtown/Magnificent Mile. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus an indoor pool and a restaurant.
Pool
Haustierfreundlich

Freehand Chicago
19 East Ohio Street, Chicago, IL
The price is CHF 97 per night
CHF 97
3 Sept - 4 Sept
includes taxes & fees
1.3 km from city centre
Our customers tell us that they can't get enough of the helpful staff at Freehand Chicago. 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.
Haustierfreundlich
Kostenloses WLAN
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.
Chicago neighborhoods
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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.