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The Loop Vacation Packages

The Loop Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $671, price is now $367 per person
$367
per person
Nov 25 - Dec 2
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions United Center and Chicago Riverwalk are located nearby.
SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

3.5 out of 5
Chinatown
Price was $852, price is now $543 per person
$543
per person
Nov 25 - Dec 2
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free breakfast, a 24-hour fitness center, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Soldier Field and Grant Park are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,226, price is now $606 per person
$606
per person
Nov 25 - Dec 2
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $980, price is now $543 per person
$543
per person
Nov 23 - Nov 29
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.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,429, price is now $848 per person
$848
per person
Nov 25 - Dec 2
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. 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
Save 100% on your flight
Price was $857, price is now $512 per person
$512
per person
Nov 23 - Nov 29
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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,307, price is now $1,389 per person
$1,389
per person
Nov 22 - Nov 27
found 13 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $804, price is now $502 per person
$502
per person
Nov 25 - Dec 2
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

3-4 Night Vacations in The Loop

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

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $442, price is now $305 per person
$305
per person
Dec 9 - Dec 12
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
Save 100% on your flight
Price was $798, price is now $479 per person
$479
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
Price was $489, price is now $332 per person
$332
per person
Dec 9 - Dec 12
found 1 day 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 $1,054, price is now $725 per person
$725
per person
Dec 9 - Dec 12
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.
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

4 out of 5
Price was $458, price is now $252 per person
$252
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was $2,445, price is now $1,340 per person
$1,340
per person
Nov 28 - Dec 3
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,226, price is now $606 per person
$606
per person
Nov 25 - Dec 2
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $671, price is now $367 per person
$367
per person
Nov 25 - Dec 2
found 24 hours 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
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
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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
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
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
85 East Wacker Drive, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
Opens in a new windowLondonHouse Chicago, Curio Collection by Hilton
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in ...
Opens in a new windowHyatt Regency 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.

Frontier Airlines
Fri, Nov 7 - Tue, Nov 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 3 days ago
$83
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Nov 7 from Los Angeles Intl. to O'Hare Intl., returning Tue, Nov 11, priced at $83 found 3 days ago
Frontier Airlines
Sat, Nov 15 - Sun, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$84 Roundtrip, found 11 hours ago
$84
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Los Angeles Intl. to O'Hare Intl., returning Sun, Nov 16, priced at $84 found 11 hours ago
Frontier Airlines
Wed, Oct 22 - Mon, Oct 27
LAX
Los Angeles Intl.
MDW
Midway Intl.
$239 Roundtrip, found 5 days ago
$239
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Oct 22 from Los Angeles Intl. to Midway Intl., returning Mon, Oct 27, priced at $239 found 5 days ago
All Nippon Airways
Wed, Nov 5 - Mon, Dec 1
PVG
Pudong Intl.
ORD
O'Hare Intl.
$999 Roundtrip, found 4 days ago
$999
Roundtrip
found 4 days ago
Select All Nippon Airways flight, departing Wed, Nov 5 from Pudong Intl. to O'Hare Intl., returning Mon, Dec 1, priced at $999 found 4 days ago