Downtown Chicago Holidays

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Top Downtown Chicago holiday packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Downtown Chicago

29 May - 2 Jun

4 night stay

Dublin (DUB) to Chicago (ORD)

Delta • Direct return • FirstClass
per person
found 1 day 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.
Virgin Hotels Chicago
4.5-star property

Virgin Hotels Chicago

Downtown Chicago

29 May - 2 Jun

4 night stay

Dublin (DUB) to Chicago (ORD)

Delta • Direct return • FirstClass
per person
found 1 day 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.
The Peninsula Chicago
5.0-star property

The Peninsula Chicago

Downtown Chicago

29 May - 2 Jun

4 night stay

Dublin (DUB) to Chicago (ORD)

Delta • Direct return • FirstClass
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.
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

Downtown Chicago

29 May - 2 Jun

4 night stay

Dublin (DUB) to Chicago (ORD)

Delta • Direct return • FirstClass
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.
The Emily Hotel
4.0-star property

The Emily Hotel

Downtown Chicago

29 May - 2 Jun

4 night stay

Dublin (DUB) to Chicago (ORD)

Delta • Direct return • FirstClass
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.

Downtown Chicago Holiday Packages for 4 Nights

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Downtown Chicago

29 May - 2 Jun

4 night stay

Dublin (DUB) to Chicago (ORD)

Delta • Direct return • FirstClass
per person
found 1 day 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.
Virgin Hotels Chicago
4.5-star property

Virgin Hotels Chicago

Downtown Chicago

29 May - 2 Jun

4 night stay

Dublin (DUB) to Chicago (ORD)

Delta • Direct return • FirstClass
per person
found 1 day 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.
The Peninsula Chicago
5.0-star property

The Peninsula Chicago

Downtown Chicago

29 May - 2 Jun

4 night stay

Dublin (DUB) to Chicago (ORD)

Delta • Direct return • FirstClass
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.
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

Downtown Chicago

29 May - 2 Jun

4 night stay

Dublin (DUB) to Chicago (ORD)

Delta • Direct return • FirstClass
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.
The Emily Hotel
4.0-star property

The Emily Hotel

Downtown Chicago

29 May - 2 Jun

4 night stay

Dublin (DUB) to Chicago (ORD)

Delta • Direct return • FirstClass
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.

Downtown Chicago Holiday Packages for 6-7 Nights

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North
4.0-star property

Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

15 May - 21 May

6 night stay

Dublin (DUB) to Chicago (ORD)

British Airways • Direct • Coach

Chicago (ORD) to Dublin (DUB)

American Airlines • Direct • Coach
per person
found 1 day ago
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.
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Downtown Chicago

15 May - 21 May

6 night stay

Dublin (DUB) to Chicago (ORD)

British Airways • Direct • Coach

Chicago (ORD) to Dublin (DUB)

American Airlines • Direct • Coach
Save 100% on your flight
per person
found 1 day 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.
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

Downtown Chicago

15 May - 21 May

6 night stay

Dublin (DUB) to Chicago (ORD)

British Airways • Direct • Coach

Chicago (ORD) to Dublin (DUB)

American Airlines • Direct • Coach
Save 100% on your flight
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.
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Downtown Chicago

15 May - 21 May

6 night stay

Dublin (DUB) to Chicago (ORD)

British Airways • Direct • Coach

Chicago (ORD) to Dublin (DUB)

American Airlines • Direct • Coach
Save 100% on your flight
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.
Virgin Hotels Chicago
4.5-star property

Virgin Hotels Chicago

Downtown Chicago

15 May - 21 May

6 night stay

Dublin (DUB) to Chicago (ORD)

British Airways • Direct • Coach

Chicago (ORD) to Dublin (DUB)

American Airlines • Direct • Coach
Save 100% on your flight
per person
found 1 day 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.

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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
The price is €100 per night
€100
includes taxes & fees
20 Apr - 21 Apr
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

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is €142 per night
€142
includes taxes & fees
13 Apr - 14 Apr
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
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr, Chicago, IL
The price is €226 per night
€226
includes taxes & fees
13 Apr - 14 Apr
0.83 km from Downtown Chicago
The sightseeing around Swissotel - Chicago gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as 2 bars, a restaurant and a 24-hour gym.
Spa
Pet-friendly
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
The price is €107 per night
€107
includes taxes & fees
20 Apr - 21 Apr
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
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is €128 per night
€128
includes taxes & fees
21 Apr - 22 Apr
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
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave, Chicago, IL
The price is €161 per night
€161
includes taxes & fees
6 Apr - 7 Apr
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
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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 Downtown Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, 14 May - Sat, 17 May
LAX
Los Angeles
ORD
Chicago
€193 Return, found 1 day ago
€193
Return
found 1 day ago
Select American Airlines flight, departing Wed, 14 May from Los Angeles to Chicago, returning Sat, 17 May, priced at €193 found 1 day ago
Tue, 8 Jul - Fri, 11 Jul
LAX
Los Angeles
MDW
Chicago
€256 Return, found 6 days ago
€256
Return
found 6 days ago
Select Delta flight, departing Tue, 8 Jul from Los Angeles to Chicago, returning Fri, 11 Jul, priced at €256 found 6 days ago
Sat, 31 May - Sat, 7 Jun
FCO
Rome
ORD
Chicago
€721 Return, found 18 hours ago
€721
Return
found 18 hours ago
Select Swiss International Air Lines flight, departing Sat, 31 May from Rome to Chicago, returning Sat, 7 Jun, priced at €721 found 18 hours ago

Holiday ideas like Downtown Chicago vacations

Other holiday destinations

^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.