Vacations from $553
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Hotel Felix River North/Magnificent Mile
Oct 16 - Oct 19Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property8.2/10 - Very Good (2,859 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop - Hotel Riu Plaza Chicago
Sep 25 - Sep 28Hotel Riu Plaza Chicago + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (4,798 reviews)"Perfect location,superb breakfast buffet, rooftop bar was outstanding and a great option for happy hour!!! We will definitely stay here again on our next trip to Chicago"Reviewed July 24, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop - Hotel Saint Clair- Magnificent Mile
Aug 26 - Aug 30Hotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago4 nights4.0 star property8.4/10 - Very Good (2,060 reviews)"Nice staff and clean space"Reviewed July 23, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Swissotel - Chicago
Sep 25 - Sep 28Swissotel - Chicago + Flight
Downtown Chicago3 nights4.5 star property9.0/10 - Wonderful (3,507 reviews)"The fact that the keep their own bees and incorporate their honey into their Food. The cocktails in the lounge and the Hummus platter were amazing. Maria was our Server all weekend, she took extremely good care of us!! Breakfast by room room service was really good and convenient. The one Thing that I didn’t like about room service was there was a two different extra charges. One was a Service Charge and one was a Convenience charge, which, really are one and the same. Seemed completely..."Reviewed July 23, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop - Level Chicago - River North
Sep 25 - Sep 28Level Chicago - River North + Flight
Downtown Chicago3 nights4.0 star property9.2/10 - Wonderful (1,040 reviews)"We had such a great stay! Only complaint was one of the blinds would not shut in one of the bedrooms, but we understood it was probably not fixable in the 2 days we were there. We were also upgraded to a better room upon arrival! Overall 10/10!"Reviewed July 23, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.