Holidays in Chicago
2 travellers
Mon 5/20
Thu 5/23
Search hundreds of travel sites at once for holiday package deals in Chicago
...and more
Let KAYAK do the searching
Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allDowntown
Free Wi-Fi
Pet-friendly
New York LaGuardia
Meals not included
3 nights + flight
$498
Downtown
Free Wi-Fi
Pool
Pet-friendly
New York LaGuardia
Meals not included
3 nights + flight
$497
Downtown
Free Wi-Fi
Pet-friendly
New York LaGuardia
Meals not included
3 nights + flight
$558
Hyatt House Chicago Medical/University District - Chicago - Building![Hyatt House Chicago Medical/University District - Chicago - Building]()
Hyatt House Chicago Medical/University District
Near West Side
Free Wi-Fi
Charlotte Douglas
Breakfast
3 nights + flight
$557
Downtown
Free Wi-Fi
Pet-friendly
Raleigh-Durham
Meals not included
3 nights + flight
$522
Sonder Jewelers Row - Chicago - Bar![Sonder Jewelers Row - Chicago - Bar]()
Sonder Jewelers Row
Downtown
Free Wi-Fi
New York LaGuardia
Meals not included
3 nights + flight
$529
The Royal Sonesta Chicago River North - Chicago - Lounge![The Royal Sonesta Chicago River North - Chicago - Lounge]()
The Royal Sonesta Chicago River North
Downtown
Free Wi-Fi
Pool
Pet-friendly
New York LaGuardia
Meals not included
3 nights + flight
$486
Downtown
Free Wi-Fi
Pool
Pet-friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$619
Downtown
Pet-friendly
New York LaGuardia
Meals not included
3 nights + flight
$494
Downtown
Free Wi-Fi
Pet-friendly
Spa
New York LaGuardia
Meals not included
3 nights + flight
$515
Downtown
Free Wi-Fi
Pool
Pet-friendly
Spa
Charlotte Douglas
Meals not included
3 nights + flight
$1,078
Downtown
Free Wi-Fi
Pool
New York LaGuardia
Meals not included
3 nights + flight
$511
Downtown
Free Wi-Fi
Pool
Pet-friendly
Spa
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$1,075
Downtown
Free Wi-Fi
Pet-friendly
New York LaGuardia
Meals not included
3 nights + flight
$457
Last minute holiday packages to Chicago
Show allDowntown
Free Wi-Fi
Pool
Pet-friendly
Boston Logan Intl
Meals not included
3 nights + flight
$781
Downtown
Free Wi-Fi
Pet-friendly
Boston Logan Intl
Meals not included
3 nights + flight
$827
When to book a holiday in Chicago
Price includes flights and 3 nights accommodation for 2 travellers. Prices are not fixed and may vary with time.
Where to stay in Chicago
Our map will help you find the perfect place to stay for your holiday in Chicago by showing you the exact location of each hotel.
Other popular package holiday destinations
- Suva, Fiji package holidays
- Yamba, NSW, Australia package holidays
- Victor Harbor, SA, Australia package holidays
- Sapporo, Japan package holidays
- Cebu City, Cebu, Philippines package holidays
- North Kuta, Bali, Indonesia package holidays
- Exmouth, WA, Australia package holidays
- Amalfi, Salerno, Italy package holidays
- Apia, Samoa package holidays
- Gympie, QLD, Australia package holidays
- Brooklyn, NY, United States package holidays
- Austin, TX, United States package holidays
- Miami Beach, FL, United States package holidays
- West Hollywood, CA, United States package holidays
- Nashville, TN, United States package holidays
- Denver, CO, United States package holidays
- Dallas, TX, United States package holidays
- Kailua-Kona, The Big Island, HI, United States package holidays
- Anchorage, AK, United States package holidays
- Houston, TX, United States package holidays