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Bloomingdale Vacation Packages

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Bloomingdale Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $556, price is now $361 per person
$361
per person
Dec 7 - Dec 11
found 1 day 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 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,005, price is now $619 per person
$619
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $742, price is now $487 per person
$487
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), 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.

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,486, price is now $982 per person
$982
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.

Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $833, price is now $552 per person
$552
per person
Dec 3 - Dec 6
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, 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.

The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $722, price is now $481 per person
$481
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.

Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
Price was $936, price is now $627 per person
$627
per person
Dec 11 - Dec 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
I loved the staff and amentias khory and the others were great. I also love the breakfast and happy hour. I would definitely visit again!

Reviewed on Oct 11, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $700, price is now $470 per person
$470
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Very comfortable bed,the staff were nice and helpful. Breakfast was delicious

Reviewed on Oct 11, 2026

Bloomingdale Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $556, price is now $361 per person
$361
per person
Dec 7 - Dec 11
found 1 day 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 $1,005, price is now $619 per person
$619
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $742, price is now $487 per person
$487
per person
Dec 7 - Dec 11
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 $1,486, price is now $982 per person
$982
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Bloomingdale Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $672, price is now $424 per person
$424
per person
Dec 11 - Dec 17
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 $2,059, price is now $1,190 per person
$1,190
per person
Nov 12 - Nov 17
found 4 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,599, price is now $927 per person
$927
per person
Nov 12 - Nov 17
found 4 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,245, price is now $754 per person
$754
per person
Dec 2 - Dec 7
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Wed, Oct 28 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$194 Roundtrip, found 2 days ago
$194
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Oct 28 from Los Angeles Intl. to O'Hare Intl., returning Sat, Nov 7, priced at $194 found 2 days ago
American Airlines
Fri, Nov 13 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, just found
$197
Roundtrip
just found
Select American Airlines flight, departing Fri, Nov 13 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 13, priced at $197 just found
Southwest Airlines
Mon, Nov 9 - Fri, Nov 13
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197 Roundtrip, found 17 hours ago
$197
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Mon, Nov 9 from Los Angeles Intl. to Midway Intl., returning Fri, Nov 13, priced at $197 found 17 hours ago
Philippine Airlines
Fri, Nov 13 - Wed, Dec 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$928 Roundtrip, found 1 hour ago
$928
Roundtrip
found 1 hour ago
Select Philippine Airlines flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Wed, Dec 2, priced at $928 found 1 hour ago