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Chicago Vacation Packages

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Chicago Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $626, price is now $407 per person
$407
per person
Apr 16 - Apr 19
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,166, price is now $621 per person
$621
per person
May 1 - May 4
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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $698, price is now $429 per person
$429
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $915, price is now $588 per person
$588
per person
May 1 - May 4
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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $778, price is now $506 per person
$506
per person
Apr 16 - Apr 19
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 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $904, price is now $593 per person
$593
per person
Mar 9 - Mar 12
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.
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $839, price is now $551 per person
$551
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $750, price is now $494 per person
$494
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.

Chicago Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $626, price is now $407 per person
$407
per person
Apr 16 - Apr 19
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 $1,166, price is now $621 per person
$621
per person
May 1 - May 4
found 1 day 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 $698, price is now $429 per person
$429
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $915, price is now $588 per person
$588
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Chicago Vacation Packages 5-7 Night Stays

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 $370, price is now $216 per person
$216
per person
Mar 18 - Mar 23
found 12 hours 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 $2,099, price is now $1,358 per person
$1,358
per person
Mar 27 - Apr 1
found 21 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $992, price is now $648 per person
$648
per person
Mar 18 - Mar 23
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Save 100% on your flight
Price was $844, price is now $565 per person
$565
per person
Mar 14 - Mar 21
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Sat, Mar 7 - Wed, Mar 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$46 Roundtrip, found 2 hours ago
$46
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Mar 7 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Mar 11, priced at $46 found 2 hours ago
Frontier Airlines
Wed, Apr 15 - Wed, May 6
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$56 Roundtrip, found 1 day ago
$56
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Apr 15 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, May 6, priced at $56 found 1 day ago
Frontier Airlines
Wed, Mar 4 - Tue, Mar 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$56 Roundtrip, found 3 hours ago
$56
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Mar 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Mar 10, priced at $56 found 3 hours ago
Frontier Airlines
Tue, Apr 28 - Fri, May 1
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$56 Roundtrip, found 1 hour ago
$56
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Apr 28 from Newark Liberty Intl. Airport to Midway Intl., returning Fri, May 1, priced at $56 found 1 hour ago