Holidays in Chicago
2 travellers
KAYAK searches hundreds of travel sites at once for holiday package deals in Chicago
...and more
Here is why travellers choose KAYAK
Free to useThere are no hidden charges or fees.
Filter your dealsFilter by free cancellation, free breakfast and more.
Millions of reviewsCheck ratings based on millions of real guest reviews.
Bundle and saveSave money when you bundle your flight + hotel.
Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allNear North Side
Pool
Pet-friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$406
Home2 Suites by Hilton Chicago River North - Chicago - Bedroom![Home2 Suites by Hilton Chicago River North - Chicago - Bedroom]()
Home2 Suites by Hilton Chicago River North
Near North Side
Free Wi-Fi
Pet-friendly
Cleveland Hopkins Intl
Breakfast
3 nights + flight
$518
Admiral Motel By OYO Chicago I-94 - Chicago - Building![Admiral Motel By OYO Chicago I-94 - Chicago - Building]()
Admiral Motel By OYO Chicago I-94
Chatham
Parking
Pet-friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$349
Mccormick Place Guest House - Chicago - Balcony![Mccormick Place Guest House - Chicago - Balcony]()
Mccormick Place Guest House
Douglas
Parking
Free Wi-Fi
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$466
Near North Side
Pool
Pet-friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$538
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
Pet-friendly
Minneapolis St Paul
Breakfast
3 nights + flight
$526
O'Hare
Airport shuttle
Pool
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$568
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$814
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool![Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool]()
Hampton Inn & Suites by Hilton Chicago Medical District UIC
Near West Side
Pool
Pet-friendly
Minneapolis St Paul
Breakfast
3 nights + flight
$519
Near North Side
Free Wi-Fi
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$485
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Denver Intl
Meals not included
3 nights + flight
$892
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$1,181
Near North Side
Free Wi-Fi
Pet-friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$711
Near North Side
Free Wi-Fi
Pet-friendly
Los Angeles
Meals not included
3 nights + flight
$629
Last minute holiday packages to Chicago
Show allO'Hare
Airport shuttle
Free Wi-Fi
Pool
Denver Intl
Meals not included
3 nights + flight
$1,037
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.
Tips for finding Chicago package deals
- There are loads of types of holidays in Chicago and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travellers: Top holiday $216; Family holiday $757; Romantic holiday $786; Luxury holiday $757; Budget holiday $786.
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.Everything you need to know for your holiday in Chicago
Complete your trip to Chicago
Other popular hotel destinations
Other popular package holiday destinations
Chicago holiday information
| Top holiday (Flight+Hotel) | $216 |
|---|---|
| Family holiday (Flight+Hotel) | $757 |
| Romantic holiday (Flight+Hotel) | $786 |
| Luxury holiday (Flight+Hotel) | $757 |
| Budget holiday (Flight+Hotel) | $786 |