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
Hotel Riu Plaza Chicago
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,304, price is now €872 per person
€872
per person
found 10 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
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Save 100% on your flight
Price was €2,050, price is now €1,323 per person
€1,323
per person
found 10 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.
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,478, price is now €1,035 per person
€1,035
per person
found 10 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
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,283, price is now €913 per person
€913
per person
found 10 hours 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
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,377, price is now €1,008 per person
€1,008
per person
found 10 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.
Downtown Chicago Holiday Packages for 5 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was €841, price is now €624 per person
€624
per person
found 3 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
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was €1,672, price is now €1,091 per person
€1,091
per person
found 4 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
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was €974, price is now €720 per person
€720
per person
found 12 hours 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
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
Lufthansa • Coach
Chicago (ORD) to Dublin (DUB)
Brussels Airlines • Coach
Price was €1,981, price is now €1,507 per person
€1,507
per person
found 2 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
Sofitel Chicago Magnificent Mile
Downtown Chicago
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was €973, price is now €768 per person
€768
per person
found 9 hours ago
Sofitel Chicago Magnificent Mile'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 a restaurant and a 24-hour gym. This property offers pet-friendly amenities, such as food and water bowls.
Downtown 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
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,304, price is now €872 per person
€872
per person
found 10 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
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Save 100% on your flight
Price was €2,050, price is now €1,323 per person
€1,323
per person
found 10 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.
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,478, price is now €1,035 per person
€1,035
per person
found 10 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
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,283, price is now €913 per person
€913
per person
found 10 hours 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
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,377, price is now €1,008 per person
€1,008
per person
found 10 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.
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
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
The price is €89 per night
€89
5 Jan - 6 Jan 2026
includes taxes & fees
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
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
The price is €152 per night
€152
2 Jan - 3 Jan 2026
includes taxes & fees
0.6 km from Downtown Chicago
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
Spa
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
The price is €81 per night
€81
7 Jan - 8 Jan 2026
includes taxes & fees
0.36 km from Downtown Chicago
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.
Pet-friendly
Free WiFi
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
0.54 km from Downtown Chicago
Our customers tell us that they can't get enough of the comfortable beds at Silversmith Hotel Chicago Downtown. 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 24-hour gym and a bar.
Free WiFi
Air conditioning
Hilton Chicago
720 S Michigan Ave Chicago IL
The price is €146 per night
€146
1 Jan - 2 Jan 2026
includes taxes & fees
1.54 km from Downtown Chicago
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
Hot tub
Eurostars Magnificent Mile
660 North State Street Chicago IL
The price is €86 per night
€86
25 Jan - 26 Jan 2026
includes taxes & fees
0.92 km from Downtown Chicago
Eurostars Magnificent Mile's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Free WiFi in public areas, a full-service spa and a gym are available.
Spa
Free WiFi
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.
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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.