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Downtown Chicago Vacation Packages

3-4 Night Vacations in Downtown Chicago

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,183, price is now $727 per person
$727
per person
Jun 5 - Jun 8
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,217, price is now $781 per person
$781
per person
Jun 5 - Jun 8
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,715, price is now $1,134 per person
$1,134
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,125, price is now $770 per person
$770
per person
Jun 5 - Jun 8
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Downtown Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,509, price is now $922 per person
$922
per person
Jun 14 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,763, price is now $958 per person
$958
per person
Jun 14 - Jun 21
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,953, price is now $1,158 per person
$1,158
per person
Jun 14 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,278, price is now $1,374 per person
$1,374
per person
Jun 9 - Jun 16
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

Cheap Hotel Deals in Downtown Chicago

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
Opens in a new windowHotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Opens in a new windowRiver Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Opens in a new windowClub Quarters Hotel, Central Loop, Chicago
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Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
Opens in a new windowHotel Riu Plaza Chicago
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Opens in a new windowHoliday Inn Chicago Dwtn - The Mart by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Opens in a new windowHilton Chicago/Magnificent Mile Suites
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Opens in a new windowCongress Plaza Hotel
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowFairmont Chicago at Millennium Park
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.

Top Flight Deals

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

Frontier Airlines
Wed, May 27 - Sat, May 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$144 Roundtrip, found 13 hours ago
$144
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Wed, May 27 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 30, priced at $144 found 13 hours ago
Frontier Airlines
Tue, May 19 - Thu, May 28
LAX
Los Angeles Intl.
MDW
Midway Intl.
$216 Roundtrip, found 3 hours ago
$216
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Tue, May 19 from Los Angeles Intl. to Midway Intl., returning Thu, May 28, priced at $216 found 3 hours ago
American Airlines
Sun, May 24 - Sun, May 31
LAX
Los Angeles Intl.
RFD
Greater Rockford
$344 Roundtrip, found 1 day ago
$344
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, May 24 from Los Angeles Intl. to Greater Rockford, returning Sun, May 31, priced at $344 found 1 day ago
Iberia
Wed, Jul 8 - Wed, Jul 22
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$826 Roundtrip, found 4 days ago
$826
Roundtrip
found 4 days ago
Select Iberia flight, departing Wed, Jul 8 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Wed, Jul 22, priced at $826 found 4 days ago