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 Felix River North/Magnificent Mile
Downtown Chicago
26 Jul - 31 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
Finnair • Return • Coach
Price was €1,785, price is now €1,273 per person
€1,273
per person
found 1 day 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.
4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
26 Jul - 31 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
Finnair • Return • Coach
Save 100% on your flight
Price was €2,960, price is now €2,051 per person
€2,051
per person
found 1 day ago
Our customers tell us that they can't get enough of the comfortable beds at LondonHouse Chicago, Curio Collection by Hilton. During your stay, you're just a quick walk from Chicago Riverwalk. Features include free WiFi in public areas, plus 2 restaurants and 2 bars.
4.0-star property
The Emily Hotel
Downtown Chicago
26 Jul - 31 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
Finnair • Return • Coach
Price was €2,178, price is now €1,560 per person
€1,560
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
26 Jul - 31 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
Finnair • Return • Coach
Save 100% on your flight
Price was €3,025, price is now €2,181 per person
€2,181
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
26 Jul - 31 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
Finnair • Return • Coach
Save 100% on your flight
Price was €3,435, price is now €2,554 per person
€2,554
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.
Downtown Chicago Holiday Packages for 5 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
26 Jul - 31 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
Finnair • Return • Coach
Price was €1,785, price is now €1,273 per person
€1,273
per person
found 1 day 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.
4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
26 Jul - 31 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
Finnair • Return • Coach
Save 100% on your flight
Price was €2,960, price is now €2,051 per person
€2,051
per person
found 1 day ago
Our customers tell us that they can't get enough of the comfortable beds at LondonHouse Chicago, Curio Collection by Hilton. During your stay, you're just a quick walk from Chicago Riverwalk. Features include free WiFi in public areas, plus 2 restaurants and 2 bars.
4.0-star property
The Emily Hotel
Downtown Chicago
26 Jul - 31 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
Finnair • Return • Coach
Price was €2,178, price is now €1,560 per person
€1,560
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
26 Jul - 31 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
Finnair • Return • Coach
Save 100% on your flight
Price was €3,025, price is now €2,181 per person
€2,181
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
26 Jul - 31 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
Finnair • Return • Coach
Save 100% on your flight
Price was €3,435, price is now €2,554 per person
€2,554
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.
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 €143 per night
€143
per night
29 Jun - 30 Jun
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
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
The price is €146 per night
€146
per night
6 Jul - 7 Jul
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 an indoor pool and a gym.
Pool
Pet-friendly
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
The price is €203 per night
€203
per night
5 Jul - 6 Jul
0.98 km from Downtown Chicago
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.
Breakfast included
Free WiFi
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
The price is €129 per night
€129
per night
1 Jul - 2 Jul
1.22 km from Downtown Chicago
The Chicago Hotel Collection - 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 2 restaurants and 2 bars.
Pet-friendly
Free WiFi
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
The price is €129 per night
€129
per night
1 Jul - 2 Jul
2.22 km from Downtown Chicago
Our customers tell us that they can't get enough of the helpful staff at The Chicago Hotel Collection Ambassador Gold Coast. During your stay, you're just a quick walk from Lake Michigan. Free WiFi in public areas, a restaurant and a 24-hour gym are available.
Pet-friendly
Free WiFi
River Hotel
75 East Wacker Drive Chicago IL
The price is €161 per night
€161
per night
30 Jun - 1 Jul
0.36 km from Downtown Chicago
Our customers tell us that they can't get enough of the helpful staff at River Hotel. 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. This property offers pet-friendly amenities, such as food and water bowls.
Pet-friendly
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.
Things to do
Chicago Sightseeing River and Lake Cruise
€37
per adult
100% of travellers recommend
Chicago By Night River and Lake Cruise
€40
per adult
94% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
€36
per adult
86% of travellers recommend
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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.