Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $1,096, price is now $591 per person
$591
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.
would definitely stay here again :)
Reviewed on Jul 15, 2026
Hotel Riu Plaza Chicago
Price was $1,507, price is now $790 per person
$790
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.
Great place and location.
Reviewed on Jul 15, 2026
Level Chicago - River North
Save 100% on your flight
Price was $1,446, price is now $811 per person
$811
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.
Holes in the carpeting in living room. Door that enters unit doesn’t close without slamming it. Looks like wear and tear since we were there before.
Reviewed on Jul 14, 2026
Hampton Inn & Suites Chicago Medical District UIC
Save 100% on your flight
Price was $1,044, price is now $599 per person
$599
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 a fitness center. Popular attractions United Center and Chicago Riverwalk are located nearby.
I enjoyed my stay here. Clean room, well maintained property and great location just 3 miles from Chicago. The best part was the friendly staff. The breakfast was a 4.5 out 5, just adequate foe the day's need, nothing super special. I would definitely return.
Reviewed on Jul 13, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,717, price is now $991 per person
$991
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 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.
Free beer no perfect everyone was great
Reviewed on Jul 15, 2026
Hotel Saint Clair- Magnificent Mile
Save 100% on your flight
Price was $1,130, price is now $693 per person
$693
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, 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.
I wish the space was bigger. It was too tight for me and my young girls but the staff was so extra nice and welcoming.
Reviewed on Jul 14, 2026
The Whitehall Hotel, BW Premier Collection
Save 100% on your flight
Price was $1,079, price is now $672 per person
$672
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 fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Fairmont Chicago at Millennium Park
Save 100% on your flight
Price was $1,392, price is now $868 per person
$868
per person
Sep 23 - Sep 28
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 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
They have a big focus on cleanliness which is great, but the absolute lack of amenities were ridiculous. No free water bottles. No free parking. The room was tiny for a Signature Room. I understand they get away with this stuff because they are located in downtown but still not sufficient for a basic hotel. I got a discounted price because of Expedia so I got saved a little bit, but I would never pay full price for this room.
Reviewed on Jul 15, 2026
Chicago Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chicago Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Aug 18 - Mon, Aug 24
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 3 days ago
$100
Roundtrip
found 3 days ago
Wed, Aug 5 - Thu, Aug 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$107 Roundtrip, just found
$107
Roundtrip
just found
Mon, Sep 28 - Thu, Oct 1
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$138 Roundtrip, found 5 days ago
$138
Roundtrip
found 5 days ago
Mon, Aug 17 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
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