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The Loop Vacation Packages

The Loop Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Prospect Heights by IHG

Holiday Inn Express & Suites Prospect Heights by IHG

3 out of 5
Save 100% on your flight
Price was $363, price is now $214 per person
$214
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Prospect Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Rob Roy Golf Course and Northbrook Sports Complex are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,029, price is now $442 per person
$442
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was $793, price is now $374 per person
$374
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $698, price is now $374 per person
$374
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $617, price is now $345 per person
$345
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Saratoga Motel By Capital O Near Midway Airport Chicago IL

Saratoga Motel By Capital O Near Midway Airport Chicago IL

2.5 out of 5
Save 100% on your flight
Price was $406, price is now $231 per person
$231
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and room service. Popular attraction SeatGeek Stadium is located nearby.
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 $422, price is now $242 per person
$242
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $967, price is now $571 per person
$571
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.

3-4 Night Vacations in The Loop

Price found within the past 48 hours. Click for updated prices.
Saratoga Motel By Capital O Near Midway Airport Chicago IL

Saratoga Motel By Capital O Near Midway Airport Chicago IL

2.5 out of 5
Save 100% on your flight
Price was $267, price is now $168 per person
$168
per person
Dec 6 - Dec 9
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $539, price is now $297 per person
$297
per person
Dec 6 - Dec 9
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $415, price is now $243 per person
$243
per person
Dec 6 - Dec 9
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,664, price is now $1,078 per person
$1,078
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in The Loop

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $617, price is now $345 per person
$345
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,029, price is now $442 per person
$442
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was $793, price is now $374 per person
$374
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $698, price is now $374 per person
$374
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Cheap Hotel Deals in The Loop

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 free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Opens in a new windowCongress Plaza Hotel
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
Opens in a new windowcitizenM Chicago Downtown
Pendry Chicago

Pendry Chicago

4.5 out of 5
230 North Michigan Avenue, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff ...
Opens in a new windowPendry Chicago
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The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar ...
Opens in a new windowThe Allegro Royal Sonesta Hotel Chicago Loop
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
71 E Wacker Dr, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
Opens in a new windowThe Royal Sonesta Chicago Downtown
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave, Chicago, IL
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Opens in a new windowHilton Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
Opens in a new windowPalmer House a Hilton Hotel
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the ...
Opens in a new windowSwissotel - Chicago
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.

Spirit Airlines
Fri, Nov 14 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 4 days ago
$134
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Fri, Nov 14 from Los Angeles Intl. to O'Hare Intl., returning Wed, Nov 19, priced at $134 found 4 days ago
American Airlines
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$189 Roundtrip, found 6 days ago
$189
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Jan 9 from Los Angeles Intl. to Greater Rockford, returning Sun, Jan 11, priced at $189 found 6 days ago
Delta
Tue, Jan 6 - Mon, Jan 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$217 Roundtrip, found 6 days ago
$217
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jan 6 from Los Angeles Intl. to Midway Intl., returning Mon, Jan 12, priced at $217 found 6 days ago
Delta
Thu, Dec 4 - Mon, Dec 15
FCO
Fiumicino - Leonardo da Vinci Intl.
MDW
Midway Intl.
$738 Roundtrip, found 2 days ago
$738
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Dec 4 from Fiumicino - Leonardo da Vinci Intl. to Midway Intl., returning Mon, Dec 15, priced at $738 found 2 days ago