Downtown Chicago Holidays
- Top Downtown Chicago holiday packages
- 3-night holiday deals
- 4-night holiday deals
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Top Downtown Chicago holiday packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
24 Apr - 28 Apr
4 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 8 hours 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 full-service spa and a 24-hour gym. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.
5.0-star property
Waldorf Astoria Chicago
Downtown Chicago
24 Apr - 28 Apr
4 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Save 100% on your flight
per person
found 8 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.
4.5-star property
Virgin Hotels Chicago
Downtown Chicago
24 Apr - 28 Apr
4 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 8 hours ago
Virgin Hotels Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. 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.
4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
24 Apr - 28 Apr
4 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 8 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.
4.0-star property
The Emily Hotel
Downtown Chicago
24 Apr - 28 Apr
4 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 8 hours ago
Our customers tell us that they can't get enough of the helpful staff at The Emily Hotel. During your stay, you'll be within walking distance of Chicago Riverwalk. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym.
Downtown Chicago Holiday Packages for 4 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
24 Apr - 28 Apr
4 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 8 hours 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 full-service spa and a 24-hour gym. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.
5.0-star property
Waldorf Astoria Chicago
Downtown Chicago
24 Apr - 28 Apr
4 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Save 100% on your flight
per person
found 8 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.
4.5-star property
Virgin Hotels Chicago
Downtown Chicago
24 Apr - 28 Apr
4 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 8 hours ago
Virgin Hotels Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. 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.
4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
24 Apr - 28 Apr
4 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 8 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.
4.0-star property
The Emily Hotel
Downtown Chicago
24 Apr - 28 Apr
4 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 8 hours ago
Our customers tell us that they can't get enough of the helpful staff at The Emily Hotel. During your stay, you'll be within walking distance of Chicago Riverwalk. 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
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
The price is €96 per night
€96
includes taxes & fees
23 Feb - 24 Feb
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
River Hotel
75 East Wacker Drive, Chicago, IL
The price is €91 per night
€91
includes taxes & fees
9 Mar - 10 Mar
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.
L7 Chicago by LOTTE
225 N Wabash Ave, Chicago, IL
The price is €155 per night
€155
includes taxes & fees
23 Feb - 24 Feb
0.28 km from Downtown Chicago
The shopping around L7 Chicago by LOTTE gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. 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.
Pet-friendly
Free WiFi
Hilton Chicago
720 S Michigan Ave, Chicago, IL
The price is €196 per night
€196
includes taxes & fees
28 Feb - 1 Mar
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
Pet-friendly
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
The price is €112 per night
€112
includes taxes & fees
23 Feb - 24 Feb
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
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
The price is €220 per night
€220
includes taxes & fees
21 Mar - 22 Mar
0.62 km from Downtown Chicago
Our customers tell us they can't get enough of Hyatt Regency Chicago's great location. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 4 restaurants and 2 bars.
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
€258 Return, found 1 day ago
€258
Return
found 1 day ago
LAX
Los Angeles
MDW
Chicago
€469 Return, found 2 days ago
€469
Return
found 2 days ago
FCO
Rome
ORD
Chicago
€565 Return, found 2 days ago
€565
Return
found 2 days ago
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^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.