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Montgomery Vacation Packages

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Montgomery Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
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 $791, price is now $510 per person
$510
per person
Sep 29 - Oct 2
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.

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Save 100% on your flight
Price was $1,169, price is now $652 per person
$652
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 free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Spacious room and very kind staffs Very close to the riverwalk and every other place to enjoy delicious food and Jazz bar

Reviewed on Jul 17, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,526, price is now $864 per person
$864
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.

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
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)
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.
Staff was amazing—so helpful, attentive, and hands-on throughout our stay. The room was absolutely gorgeous, and the view was beautiful. Everything exceeded our expectations, and we had a wonderful experience!

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 12 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

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Save 100% on your flight
Price was $1,039, price is now $637 per person
$637
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.
Very convenient when you miss a connection and have to stay overnight in Chicago!

Reviewed on Jul 17, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,061, price is now $695 per person
$695
per person
Oct 4 - Oct 7
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.
Excellent location. Staff very nice. Room big and bed very comfortable. But noisy. As is all of Chicago. Trying to sell in room soap products for exorbitant prices tachy as hell. Rooftop lounge had sadly very short hours and limited open days. Seems a shame to waste such an opportunity.

Reviewed on Jul 14, 2026

Montgomery Vacation Packages 3-4 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 $696, price is now $433 per person
$433
per person
Oct 4 - Oct 7
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 $1,237, price is now $751 per person
$751
per person
Sep 25 - Sep 29
found 12 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 $740, price is now $453 per person
$453
per person
Sep 29 - Oct 2
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 $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)

Montgomery Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,169, price is now $652 per person
$652
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 $1,526, price is now $864 per person
$864
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)
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,154, price is now $678 per person
$678
per person
Sep 23 - Sep 28
just found
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 4 days ago
$157
Roundtrip
found 4 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 4 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
Frontier Airlines
Thu, Aug 27 - Sat, Aug 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Aug 27 from Los Angeles Intl. to Midway Intl., returning Sat, Aug 29, priced at $248 found 1 day 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