
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.

4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
3 Aug - 9 Aug
6 night stay
Helsinki (HEL) to Chicago (ORD)
Iberia • Coach
Chicago (ORD) to Helsinki (HEL)
American Airlines • Coach
per person
found 5 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
3 Aug - 9 Aug
6 night stay
Helsinki (HEL) to Chicago (ORD)
Iberia • Coach
Chicago (ORD) to Helsinki (HEL)
American Airlines • Coach
per person
found 5 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.

5.0-star property
Park Hyatt Chicago
Downtown Chicago
3 Aug - 9 Aug
6 night stay
Helsinki (HEL) to Chicago (ORD)
Iberia • Coach
Chicago (ORD) to Helsinki (HEL)
American Airlines • Coach
per person
found 5 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.

5.0-star property
Waldorf Astoria Chicago
Downtown Chicago
3 Aug - 9 Aug
6 night stay
Helsinki (HEL) to Chicago (ORD)
Iberia • Coach
Chicago (ORD) to Helsinki (HEL)
American Airlines • Coach
per person
found 5 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
The Peninsula Chicago
Downtown Chicago
3 Aug - 9 Aug
6 night stay
Helsinki (HEL) to Chicago (ORD)
Iberia • Coach
Chicago (ORD) to Helsinki (HEL)
American Airlines • Coach
per person
found 5 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.
Chicago Holiday Packages for 6-7 Nights
Price found within the past 48 hours. Click for updated prices.

4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
3 Aug - 9 Aug
6 night stay
Helsinki (HEL) to Chicago (ORD)
Iberia • Coach
Chicago (ORD) to Helsinki (HEL)
American Airlines • Coach
per person
found 5 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
3 Aug - 9 Aug
6 night stay
Helsinki (HEL) to Chicago (ORD)
Iberia • Coach
Chicago (ORD) to Helsinki (HEL)
American Airlines • Coach
per person
found 5 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.

5.0-star property
Park Hyatt Chicago
Downtown Chicago
3 Aug - 9 Aug
6 night stay
Helsinki (HEL) to Chicago (ORD)
Iberia • Coach
Chicago (ORD) to Helsinki (HEL)
American Airlines • Coach
per person
found 5 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.

5.0-star property
Waldorf Astoria Chicago
Downtown Chicago
3 Aug - 9 Aug
6 night stay
Helsinki (HEL) to Chicago (ORD)
Iberia • Coach
Chicago (ORD) to Helsinki (HEL)
American Airlines • Coach
per person
found 5 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
The Peninsula Chicago
Downtown Chicago
3 Aug - 9 Aug
6 night stay
Helsinki (HEL) to Chicago (ORD)
Iberia • Coach
Chicago (ORD) to Helsinki (HEL)
American Airlines • Coach
per person
found 5 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.
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 Art Institute of Chicago. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
Ilmainen Wi-Fi
Ravintola

InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
1.21 km from city centre
Our customers tell us they can't get enough of InterContinental Chicago Magnificent Mile by IHG's great location. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 2 restaurants and an indoor pool.
Uima-allas
Kylpylä

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
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.
Lemmikkiystävällinen
Ilmainen Wi-Fi

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
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.
Uima-allas
Aamiainen sisältyy hintaan

citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
0.73 km from city centre
The sightseeing around citizenM Chicago Downtown gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Free WiFi in public areas, a restaurant and a gym are available.
Ilmainen Wi-Fi
Ravintola

The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl, Chicago, IL
2.04 km from city centre
The Whitehall Hotel, BW Premier Collection's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Free breakfast, free WiFi in public areas and a restaurant are available.
Aamiainen sisältyy hintaan
Lemmikkiystävällinen
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.
ATL
Atlanta
ORD
Chicago
€140 Return, found 4 days ago
€140
Return
found 4 days ago
LGA
New York
ORD
Chicago
€165 Return, found 2 days ago
€165
Return
found 2 days ago
JFK
New York
ORD
Chicago
€173 Return, found 1 day ago
€173
Return
found 1 day ago
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^Savings based on all package bookings with Flight + Hotel made on ebookers.fi 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.