Search Deals on
Chicago Vacation Packages

Build your package with 2 more options

Chicago Flight + Hotel Packages

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
Save 100% on your flight
Price was $475, price is now $312 per person
$312
per person
Dec 3 - Dec 6
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.
Loved the location!

Reviewed on Sep 7, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $737, price is now $428 per person
$428
per person
Dec 3 - Dec 6
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.
The only thing missing is a pool

Reviewed on Sep 7, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,316, price is now $805 per person
$805
per person
Nov 12 - Nov 15
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.
Loved it

Reviewed on Sep 7, 2026

The Wade

The Wade

4.5 out of 5
Save 100% on your flight
Price was $663, price is now $415 per person
$415
per person
Dec 3 - Dec 6
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 room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
Save 100% on your flight
Price was $988, price is now $640 per person
$640
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
All staff and workers were extremely helpful and nice, the place was extremely clean and beautiful and will be staying again

Reviewed on Sep 7, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,455, price is now $950 per person
$950
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Loved the hotel, super nice and clean! Felt like home away from home!

Reviewed on Sep 1, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $481, price is now $320 per person
$320
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The hotel was perfectly fine for a room price half the cost we paid

Reviewed on Sep 6, 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 $2,450, price is now $1,645 per person
$1,645
per person
Oct 11 - Oct 17
found 2 days 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.
.

Reviewed on Sep 7, 2026

Chicago Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $663, price is now $415 per person
$415
per person
Dec 3 - Dec 6
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 $737, price is now $428 per person
$428
per person
Dec 3 - Dec 6
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 $1,316, price is now $805 per person
$805
per person
Nov 12 - Nov 15
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 $1,068, price is now $671 per person
$671
per person
Oct 29 - Nov 2
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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,144, price is now $711 per person
$711
per person
Nov 23 - Nov 30
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 $1,570, price is now $909 per person
$909
per person
Nov 23 - Nov 30
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 $1,801, price is now $1,122 per person
$1,122
per person
Oct 21 - Oct 26
found 24 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 $1,487, price is now $931 per person
$931
per person
Oct 28 - Nov 3
found 22 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
Wed, Oct 14 - Wed, Oct 28
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 1 hour ago
$63
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 28, priced at $63 found 1 hour ago
Frontier Airlines
Sat, Oct 10 - Wed, Oct 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$80 Roundtrip, found 7 hours ago
$80
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Oct 10 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Oct 28, priced at $80 found 7 hours ago
Frontier Airlines
Thu, Oct 29 - Mon, Nov 16
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$85 Roundtrip, found 7 hours ago
$85
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, Oct 29 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Nov 16, priced at $85 found 7 hours ago
Frontier Airlines
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Oct 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $138 just found