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.
3.5-star property
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
17 Sept - 21 Sept
4 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,373, price is now €974 per person
€974
per person
found 1 day ago
The Whitehall Hotel, BW Premier Collection'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 restaurant and a gym are available.
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
17 Sept - 21 Sept
4 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Save 100% on your flight
Price was €2,193, price is now €1,406 per person
€1,406
per person
found 1 day 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
Level Chicago Fulton Market
Downtown Chicago
2 Oct - 8 Oct
6 night stay
Tirana (TIA) to Chicago (ORD)
British Airways • Direct return • Coach
Price was €2,169, price is now €1,420 per person
€1,420
per person
found 1 day ago
During your stay at Level Chicago Fulton Market, you're just a quick walk from Milwaukee Avenue. Free WiFi in public areas, a gym and a business centre are available. This property offers pet-friendly amenities, such as an off-lead area.
4.0-star property
Silversmith Hotel Chicago Downtown
Downtown Chicago
6 Oct - 11 Oct
5 night stay
Tirana (TIA) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was €2,684, price is now €1,846 per person
€1,846
per person
found 1 day ago
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 Grant Park. You'll find features such as free WiFi in public areas, plus a 24-hour gym and a bar.
4.0-star property
Eurostars Magnificent Mile
Downtown Chicago
6 Oct - 11 Oct
5 night stay
Tirana (TIA) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was €2,253, price is now €1,627 per person
€1,627
per person
found 1 day ago
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.
Downtown Chicago Holiday Packages for 4 Nights
Price found within the past 48 hours. Click for updated prices.
3.5-star property
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
17 Sept - 21 Sept
4 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,373, price is now €974 per person
€974
per person
found 1 day ago
The Whitehall Hotel, BW Premier Collection'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 restaurant and a gym are available.
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
17 Sept - 21 Sept
4 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Save 100% on your flight
Price was €2,193, price is now €1,406 per person
€1,406
per person
found 1 day 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
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
17 Sept - 21 Sept
4 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,650, price is now €1,216 per person
€1,216
per person
found 1 day 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 Navy Pier. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
17 Sept - 21 Sept
4 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,458, price is now €1,090 per person
€1,090
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
17 Sept - 21 Sept
4 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,589, price is now €1,194 per person
€1,194
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 Michigan Avenue. Features include free WiFi in public areas, plus 2 restaurants and 2 bars.
Downtown Chicago Holiday Packages for 5 Nights
Price found within the past 48 hours. Click for updated prices.
3.5-star property
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
20 Sept - 25 Sept
5 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Return • Coach
Price was €994, price is now €596 per person
€596
per person
found 12 hours ago
The Whitehall Hotel, BW Premier Collection'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 restaurant and a gym are available.
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
20 Sept - 25 Sept
5 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Return • Coach
Price was €1,606, price is now €992 per person
€992
per person
found 8 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 Navy Pier. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
24 Sept - 29 Sept
5 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Return • Coach
Price was €1,095, price is now €677 per person
€677
per person
found 8 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
Silversmith Hotel Chicago Downtown
Downtown Chicago
6 Oct - 11 Oct
5 night stay
Tirana (TIA) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was €2,684, price is now €1,846 per person
€1,846
per person
found 1 day ago
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 Grant Park. You'll find features such as free WiFi in public areas, plus a 24-hour gym and a bar.
4.0-star property
Eurostars Magnificent Mile
Downtown Chicago
6 Oct - 11 Oct
5 night stay
Tirana (TIA) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was €2,253, price is now €1,627 per person
€1,627
per person
found 1 day ago
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.
Downtown Chicago Holiday Packages for 6-7 Nights
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
2 Oct - 8 Oct
6 night stay
Tirana (TIA) to Chicago (ORD)
British Airways • Direct return • Coach
Price was €1,636, price is now €1,252 per person
€1,252
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at Holiday Inn & Suites Chicago - Downtown by IHG. During your stay, you're just a quick walk from University of Illinois Chicago. You'll find features such as free WiFi in public areas, plus a 24-hour gym and a snack bar/deli.
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
2 Oct - 8 Oct
6 night stay
Tirana (TIA) to Chicago (ORD)
British Airways • Direct return • Coach
Price was €2,169, price is now €1,420 per person
€1,420
per person
found 1 day ago
During your stay at Level Chicago Fulton Market, you're just a quick walk from Milwaukee Avenue. Free WiFi in public areas, a gym and a business centre are available. This property offers pet-friendly amenities, such as an off-lead area.
4.5-star property
Pendry Chicago
Downtown Chicago
2 Oct - 8 Oct
6 night stay
Tirana (TIA) to Chicago (ORD)
British Airways • Direct return • Coach
Price was €2,752, price is now €1,864 per person
€1,864
per person
found 1 day 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.
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 €118 per night
€118
8 Sept - 9 Sept
includes taxes & fees
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 Grant Park. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
Free WiFi
Restaurant
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
The price is €147 per night
€147
30 Aug - 31 Aug
includes taxes & fees
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
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
The price is €212 per night
€212
10 Sept - 11 Sept
includes taxes & fees
0.38 km from Downtown Chicago
Our customers tell us they can't get enough of The Allegro Royal Sonesta Hotel Chicago Loop's great location. During your stay, you're just a quick walk from Chicago Riverwalk. Features include free WiFi in public areas, plus a 24-hour gym and a bar. This property offers pet-friendly amenities, such as food and water bowls.
Hilton Chicago
720 S Michigan Ave Chicago IL
The price is €200 per night
€200
7 Sept - 8 Sept
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 Grant Park. Features include free WiFi in public areas, plus 2 restaurants and an indoor pool.
Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
The price is €297 per night
€297
2 Sept - 3 Sept
includes taxes & fees
0.68 km from Downtown Chicago
Our customers tell us that they can't get enough of the sightseeing around Fairmont Chicago at Millennium Park. 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 bars and a full-service spa. This property offers pet-friendly amenities, such as food and water bowls.
Spa
Pet-friendly
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
The price is €258 per night
€258
12 Aug - 13 Aug
includes taxes & fees
1.04 km from Downtown Chicago
Our customers tell us that they can't get enough of the shopping around Omni Chicago Hotel. During your stay, you're just a quick walk from Michigan Avenue. Free WiFi in public areas, a restaurant and a 24-hour gym are available.
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: Willis Tower Skydeck and The Ledge Ticket
€41
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
€22
per adult
90% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
€36
per adult
94% of travellers recommend
Holiday ideas like Downtown Chicago vacations
Other holiday destinations
Plan your trip to Downtown Chicago
Top Trending
Hotels
- Cheap Hotels in Farakka
- Cheap Hotels in County Fermanagh
- B&B Frenchpark
- Country House Adrigole
- Dom Jose Beach Hotel
- Dunstanburgh Castle hotels
- Cheap Hotels in North Myrtle Beach
- B&B Drumshanbo
- Jack's Place Beautiful 3-bed House Donegal
- Cheap Hotels in Delvin
- Kilt Rock hotels
- Hotel Moré
- Anastasia Waterpark Beach Resort
- Hotels in Balham
- Guest Houses Monterosso al Mare
- Hotel Best Benalmádena
- Hotels in New Brighton
- Santa Eulalia Beach hotels
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.