Downtown Chicago Holidays
- Top Downtown Chicago holiday packages
- 3-night holiday deals
- 4-night holiday deals
- 5-night holiday deals
- 6 or 7-night holiday deals
Top Downtown Chicago holiday packages
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
9 Oct - 12 Oct
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 9 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.
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9 Oct - 12 Oct
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
Save 100% on your flight
per person
found 9 hours 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.
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
9 Oct - 12 Oct
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
Save 100% on your flight
per person
found 9 hours ago
Hotel Felix River North/Magnificent Mile's great location 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 24-hour gym and a bar.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9 Oct - 12 Oct
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
Save 100% on your flight
per person
found 9 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
9 Oct - 12 Oct
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 9 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.
Downtown Chicago Holiday Packages for 3 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
9 Oct - 12 Oct
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 9 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.
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9 Oct - 12 Oct
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
Save 100% on your flight
per person
found 9 hours 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.
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
9 Oct - 12 Oct
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
Save 100% on your flight
per person
found 9 hours ago
Hotel Felix River North/Magnificent Mile's great location 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 24-hour gym and a bar.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9 Oct - 12 Oct
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
Save 100% on your flight
per person
found 9 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
9 Oct - 12 Oct
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 9 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.
Downtown Chicago Holiday Packages for 4 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
10 Oct - 14 Oct
4 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct • Coach
Chicago (ORD) to Dublin (DUB)
Iberia • Direct • Coach
Save 100% on your flight
per person
found 9 hours ago
Hotel Felix River North/Magnificent Mile's great location 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 24-hour gym and a bar.
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
10 Oct - 14 Oct
4 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct • Coach
Chicago (ORD) to Dublin (DUB)
Iberia • Direct • Coach
Save 100% on your flight
per person
found 9 hours 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
Trump International Hotel & Tower Chicago
Downtown Chicago
10 Oct - 14 Oct
4 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct • Coach
Chicago (ORD) to Dublin (DUB)
Iberia • Direct • Coach
Save 100% on your flight
per person
found 9 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
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
10 Oct - 14 Oct
4 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct • Coach
Chicago (ORD) to Dublin (DUB)
Iberia • Direct • Coach
Save 100% on your flight
per person
found 9 hours ago
Our customers tell us they can't get enough of Staypineapple, An Iconic Hotel, The Loop's great location. During your stay, you're just a quick walk from Michigan Avenue. A restaurant, a gym and a bar are available. This property offers pet-friendly amenities, such as food and water bowls.
5.0-star property
Park Hyatt Chicago
Downtown Chicago
10 Oct - 14 Oct
4 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct • Coach
Chicago (ORD) to Dublin (DUB)
Iberia • Direct • Coach
Save 100% on your flight
per person
found 9 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.
Downtown Chicago Holidays
Ready to revitalize your mind, body and spirit with some Downtown Chicago magic? The team at ebookers are experienced at making holiday fantasies into precious memories.
You want your sheets off-white and your breakfast on a rooftop? Too easy. With over 500 partner airlines and more than 500,000 worldwide properties to browse though, the world is at your feet.
Our Price Guarantee means that if you secure a Flight + Hotel package with ebookers, and then spot a better deal elsewhere within 48 hours pre check in, we'll match it and repay the difference. What's holding you back?
The time is now! Chase your inner adventurer and never let go. Every place is bursting with surprises and new things to uncover, so allow us to help you get there.Terms and Conditions apply.
More Downtown Chicago hotels
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
The price is €177 per night
€177
per night
4 Aug - 5 Aug
1.26 km from Downtown Chicago
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.
Free WiFi
Restaurant
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
The price is €271 per night
€271
per night
22 Aug - 23 Aug
0.73 km from Downtown Chicago
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.
Pool
Spa
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
The price is €143 per night
€143
per night
24 Aug - 25 Aug
1.65 km from Downtown Chicago
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.
Pet-friendly
Free WiFi
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
The price is €160 per night
€160
per night
24 Aug - 25 Aug
1.58 km from Downtown Chicago
Our customers tell us that they can't get enough of the helpful staff at Crowne Plaza Chicago West Loop by IHG. During your stay, you're just a quick walk from University of Illinois Chicago. Features include free WiFi in public areas, plus a restaurant and a gym.
Pet-friendly
Free WiFi
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €164 per night
€164
per night
24 Aug - 25 Aug
0.76 km from Downtown Chicago
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
Breakfast included
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
The price is €177 per night
€177
per night
24 Aug - 25 Aug
0.37 km from Downtown Chicago
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.
Free WiFi
Restaurant
Don't see what you're looking for?
See all available properties in Downtown Chicago
View all propertiesLowest 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 Downtown Chicago
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
LAX
Los Angeles
ORD
Chicago
€176 Return, found 2 days ago
€176
Return
found 2 days ago
LAX
Los Angeles
MDW
Chicago
€186 Return, found 1 day ago
€186
Return
found 1 day ago
LAX
Los Angeles
ORD
Chicago
€249 Return, found 1 day ago
€249
Return
found 1 day ago
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Flights
^Savings based on all package bookings with Flight + Hotel made on ebookers.ie 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.