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Paxton Vacation Packages

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Paxton Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was $672, price is now $458 per person
$458
per person
Sep 24 - Sep 28
found 21 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicagoland Speedway and Route 66 Raceway are located nearby.
It was a wonderful experience.

Reviewed on Jul 16, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,531, price is now $869 per person
$869
per person
Sep 23 - Sep 28
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 $1,091, price is now $645 per person
$645
per person
Sep 23 - Sep 28
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.
decent property - definitely shows better in photos. that was probably my biggest let-down. also, only staying one night, the room cleaner came into our room at 8 am despite check out time not being until noon. my kid was still asleep and I was in the shower. front desk service level definitely elevated the rating.

Reviewed on Jul 17, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,450, price is now $862 per person
$862
per person
Sep 23 - Sep 28
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. Our guests praise the helpful staff in our reviews. 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 $1,237, price is now $751 per person
$751
per person
Sep 25 - Sep 29
found 8 hours 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.
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.

Reviewed on Jul 14, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,304, price is now $832 per person
$832
per person
Sep 27 - Oct 1
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.

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 $1,041, price is now $688 per person
$688
per person
Sep 27 - Oct 1
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.

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Save 100% on your flight
Price was $1,044, price is now $712 per person
$712
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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 Fashion Outlets of Chicago and Rosemont Theatre are located nearby.

Paxton Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $934, price is now $593 per person
$593
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $3,287, price is now $1,969 per person
$1,969
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,237, price is now $751 per person
$751
per person
Sep 25 - Sep 29
found 8 hours 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 $986, price is now $609 per person
$609
per person
Sep 27 - Oct 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Paxton Vacation Packages 5-7 Night Stays

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
Downtown Chicago
Save 100% on your flight
Price was $1,091, price is now $645 per person
$645
per person
Sep 23 - Sep 28
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 $1,531, price is now $869 per person
$869
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,643, price is now $932 per person
$932
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,450, price is now $862 per person
$862
per person
Sep 23 - Sep 28
found 1 day 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
Tue, Aug 18 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Los Angeles Intl. to O'Hare Intl., returning Wed, Sep 2, priced at $157 found 3 days ago
United
Tue, Aug 18 - Thu, Aug 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$207 Roundtrip, found 6 days ago
$207
Roundtrip
found 6 days ago
Select United flight, departing Tue, Aug 18 from Los Angeles Intl. to O'Hare Intl., returning Thu, Aug 20, priced at $207 found 6 days ago
American Airlines
Sat, Aug 22 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$272 Roundtrip, found 7 hours ago
$272
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sat, Aug 22 from Los Angeles Intl. to O'Hare Intl., returning Wed, Sep 2, priced at $272 found 7 hours ago
Turkish Airlines
Tue, Sep 1 - Fri, Sep 18
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,190 Roundtrip, found 2 days ago
$1,190
Roundtrip
found 2 days ago
Select Turkish Airlines flight, departing Tue, Sep 1 from Capital Intl. to O'Hare Intl., returning Fri, Sep 18, priced at $1,190 found 2 days ago