Holidays in Chicago

Holidays in Chicago

2 travellers

KAYAK searches hundreds of travel sites at once for holiday package deals in Chicago

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.

Search
Best Deals
Tips
Vacation information

Cheap Chicago package deals

Go to map

Search by stars

2+ stars3+ stars4+ stars5 stars

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by board

BreakfastHalf boardSelf cateringAll-inclusiveMeals not included

Search by price

$295 - $669$669 - $1,042$1,042 - $1,416$1,416 - $1,791$1,791+ per night

Search by freebies

Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

Show all
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet-friendly
Baltimore/Washington
Meals not included
3 nights + flight
$364
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lounge
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lounge
Residence Inn by Marriott Chicago Downtown Magnificent Mile
9.1 Wonderful
Near North Side
Free Wi-Fi
Pet-friendly
Baltimore/Washington
Breakfast
3 nights + flight
$330
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG
8 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Baltimore/Washington
Breakfast
3 nights + flight
$469
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8.2 Very Good
O'Hare
Airport shuttle
Pool
Baltimore/Washington
Meals not included
3 nights + flight
$461
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown
8.3 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$697
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Raleigh-Durham
Meals not included
3 nights + flight
$1,113
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Baltimore/Washington
Meals not included
3 nights + flight
$731
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
9.3 Wonderful
Near West Side
Pool
Pet-friendly
Nashville Intl
Breakfast
3 nights + flight
$684
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
8.6 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Baltimore/Washington
Meals not included
3 nights + flight
$491
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
7.9 Good
Loop
Pool
Pet-friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$1,790
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop
8.9 Very Good
Loop
Free Wi-Fi
Pet-friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$565
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Fort Lauderdale
Meals not included
3 nights + flight
$643
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Lobby
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Lobby
The Allegro Royal Sonesta Hotel Chicago Loop
8.4 Very Good
Loop
Pet-friendly
Baltimore/Washington
Meals not included
3 nights + flight
$468
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.3 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$793
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.1 Very Good
Near North Side
Free Wi-Fi
Pool
Baltimore/Washington
Meals not included
3 nights + flight
$590
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.8 Very Good
Near North Side
Free Wi-Fi
Pool
Spa
Nashville Intl
Meals not included
3 nights + flight
$1,325

All inclusive holiday packages to Chicago

Show all
The Wheeler Mansion - Chicago - Dining room
The Wheeler Mansion - Chicago - Dining room
The Wheeler Mansion
9.8 Wonderful
Near South Side
Free Wi-Fi
Los Angeles Los Angeles
All-inclusive
3 nights + flight
$1,212

Last minute holiday packages to Chicago

Show all
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
San Juan Luis Munoz Marin Intl
Meals not included
3 nights + flight
$1,125
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.8 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
San Juan Luis Munoz Marin Intl
Breakfast
3 nights + flight
$971

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 $210; Family holiday $734; Romantic holiday $762; Luxury holiday $734; Budget holiday $762.

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

Chicago holiday information

Top holiday (Flight+Hotel)$210
Family holiday (Flight+Hotel)$734
Romantic holiday (Flight+Hotel)$762
Luxury holiday (Flight+Hotel)$734
Budget holiday (Flight+Hotel)$762