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
Arlo Chicago
Downtown Chicago
26 Dec - 2 Jan
7 night stay
Geneva (GVA) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'086, price is now CHF 790 per person
CHF 790
per person
found 1 day ago
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.
4.5-star property
Pendry Chicago
Downtown Chicago
26 Dec - 2 Jan
7 night stay
Geneva (GVA) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'371, price is now CHF 911 per person
CHF 911
per person
found 1 day ago
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.
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
26 Dec - 2 Jan
7 night stay
Geneva (GVA) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'184, price is now CHF 845 per person
CHF 845
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at Hilton Grand Vacations Club Chicago Magnificent Mile. 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.
4.5-star property
theWit Chicago, a Hilton Hotel
Downtown Chicago
26 Dec - 2 Jan
7 night stay
Geneva (GVA) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'139, price is now CHF 834 per person
CHF 834
per person
found 1 day ago
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.
4.0-star property
Hilton Orrington / Evanston
Downtown Evanston
26 Dec - 2 Jan
7 night stay
Geneva (GVA) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'129, price is now CHF 834 per person
CHF 834
per person
found 1 day ago
Our customers tell us they can't get enough of Hilton Orrington / Evanston's great location. During your stay, you'll be within walking distance of Halim Time & Glass Museum. Enjoy features like 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 Holiday Packages for 3 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
24 Nov - 27 Nov
3 night stay
Zürich (ZRH) to Chicago (ORD)
SAS • Direct return • Coach
Price was CHF 732, price is now CHF 587 per person
CHF 587
per person
found 1 day 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
24 Nov - 27 Nov
3 night stay
Zürich (ZRH) to Chicago (ORD)
SAS • Direct return • Coach
Price was CHF 1'164, price is now CHF 822 per person
CHF 822
per person
found 1 day 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.
5.0-star property
The Langham, Chicago
Downtown Chicago
24 Nov - 27 Nov
3 night stay
Zürich (ZRH) to Chicago (ORD)
SAS • Direct return • Coach
Price was CHF 1'299, price is now CHF 964 per person
CHF 964
per person
found 1 day ago
Our customers tell us they can't get enough of The Langham, Chicago's great location. During your stay, you're just a quick walk from Chicago Riverwalk. Enjoy features like 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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
24 Nov - 27 Nov
3 night stay
Zürich (ZRH) to Chicago (ORD)
Iberia • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
British Airways • Direct • Coach
Price was CHF 1'618, price is now CHF 1'201 per person
CHF 1'201
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
24 Nov - 27 Nov
3 night stay
Zürich (ZRH) to Chicago (ORD)
SAS • Direct return • Coach
Price was CHF 1'371, price is now CHF 1'032 per person
CHF 1'032
per person
found 1 day 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.
Chicago Holiday Packages for 4 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Arlo Chicago
Downtown Chicago
20 Nov - 24 Nov
4 night stay
Zürich (ZRH) to Chicago (ORD)
SAS • Direct return • Coach
Price was CHF 862, price is now CHF 586 per person
CHF 586
per person
found 1 day ago
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.
4.0-star property
The Emily Hotel
Downtown Chicago
20 Nov - 24 Nov
4 night stay
Zürich (ZRH) to Chicago (ORD)
SAS • Direct return • Coach
Price was CHF 1'138, price is now CHF 762 per person
CHF 762
per person
found 1 day ago
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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
23 Nov - 27 Nov
4 night stay
Zürich (ZRH) to Chicago (ORD)
TAP Portugal • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
British Airways • Direct • Coach
Price was CHF 1'868, price is now CHF 1'322 per person
CHF 1'322
per person
found 23 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
Pendry Chicago
Downtown Chicago
10 Dec - 14 Dec
4 night stay
Zürich (ZRH) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 902, price is now CHF 659 per person
CHF 659
per person
found 1 day ago
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.
4.5-star property
theWit Chicago, a Hilton Hotel
Downtown Chicago
20 Nov - 24 Nov
4 night stay
Zürich (ZRH) to Chicago (ORD)
SAS • Direct return • Coach
Price was CHF 845, price is now CHF 618 per person
CHF 618
per person
found 1 day ago
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.
Chicago Holiday Packages for 5 Nights
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
22 Nov - 27 Nov
5 night stay
Zürich (ZRH) to Chicago (ORD)
SAS • Direct return • Coach
Price was CHF 920, price is now CHF 669 per person
CHF 669
per person
found 23 hours ago
Our customers tell us that they can't get enough of the helpful staff at Hilton Grand Vacations Club Chicago Magnificent Mile. 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.
4.5-star property
Pendry Chicago
Downtown Chicago
22 Nov - 27 Nov
5 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 1'990, price is now CHF 1'432 per person
CHF 1'432
per person
found 1 day ago
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.
5.0-star property
The Peninsula Chicago
Downtown Chicago
22 Nov - 27 Nov
5 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 2'207, price is now CHF 1'601 per person
CHF 1'601
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.
4.5-star property
Swissotel - Chicago
Downtown Chicago
22 Nov - 27 Nov
5 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 1'009, price is now CHF 738 per person
CHF 738
per person
found 23 hours ago
The sightseeing around Swissotel - Chicago gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as 2 bars, a restaurant and a 24-hour gym.
4.0-star property
Arlo Chicago
Downtown Chicago
22 Nov - 27 Nov
5 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 920, price is now CHF 674 per person
CHF 674
per person
found 23 hours ago
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 6-7 Nights
Price found within the past 48 hours. Click for updated prices.
4.5-star property
theWit Chicago, a Hilton Hotel
Downtown Chicago
21 Nov - 27 Nov
6 night stay
Zürich (ZRH) to Chicago (ORD)
SAS • Direct return • Coach
Price was CHF 958, price is now CHF 675 per person
CHF 675
per person
found 19 hours ago
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.
4.5-star property
Pendry Chicago
Downtown Chicago
26 Dec - 2 Jan
7 night stay
Geneva (GVA) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'371, price is now CHF 911 per person
CHF 911
per person
found 1 day ago
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.
4.0-star property
The Emily Hotel
Downtown Chicago
21 Nov - 27 Nov
6 night stay
Zürich (ZRH) to Chicago (ORD)
SAS • Direct return • Coach
Price was CHF 1'085, price is now CHF 746 per person
CHF 746
per person
found 19 hours ago
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.
4.0-star property
Arlo Chicago
Downtown Chicago
21 Nov - 27 Nov
6 night stay
Zürich (ZRH) to Chicago (ORD)
British Airways • Direct return • Coach
Price was CHF 1'025, price is now CHF 723 per person
CHF 723
per person
found 23 hours ago
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.
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
26 Dec - 2 Jan
7 night stay
Geneva (GVA) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'184, price is now CHF 845 per person
CHF 845
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at Hilton Grand Vacations Club Chicago Magnificent Mile. 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.
Best Chicago hotel deals for your holiday
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
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 158 per night
CHF 158
5 Nov - 6 Nov
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
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
The price is CHF 135 per night
CHF 135
3 Nov - 4 Nov
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 a gym and a business centre.
Haustierfreundlich
Kostenloses WLAN
Freehand Chicago
19 East Ohio Street, Chicago, IL
The price is CHF 95 per night
CHF 95
5 Nov - 6 Nov
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
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
The price is CHF 164 per night
CHF 164
20 Oct - 21 Oct
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
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
The price is CHF 120 per night
CHF 120
5 Nov - 6 Nov
includes taxes & fees
1.61 km from city centre
Our customers tell us they can't get enough of Warwick Allerton - Chicago's great location. 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 24-hour gym and a bar.
Kostenloses WLAN
Klimaanlage
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.
JFK
New York
ORD
Chicago
CHF 110 Return, found 1 day ago
CHF 110
Return
found 1 day ago
JFK
New York
ORD
Chicago
CHF 126 Return, found 1 day ago
CHF 126
Return
found 1 day ago
JFK
New York
ORD
Chicago
CHF 131 Return, found 1 day ago
CHF 131
Return
found 1 day ago
Chicago neighborhoods
Other holiday destinations
Plan your trip to Chicago
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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.
