Vacations in Chicago

Vacations in Chicago

2 travelers

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

Here is why travelers 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

These are the best prices for Aug 10 - 13.
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

$212 - $472$472 - $731$731 - $991$991 - $1,250$1,250+ 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
$525
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG
8.1 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Toronto Island
Meals not included
3 nights + flight
$577
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
2.7 Poor
Chatham
Parking
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
$260
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.4 Very good
Loop
Free Wi-Fi
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$485
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
Nashville Intl
Meals not included
3 nights + flight
$463
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Los Angeles
Meals not included
3 nights + flight
$778
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Minneapolis St Paul
Meals not included
3 nights + flight
$477
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
Los Angeles
Meals not included
3 nights + flight
$548
Hotel Felix - Chicago - Lobby
Hotel Felix - Chicago - Lobby
Hotel Felix
7.7 Good
Near North Side
Free Wi-Fi
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
$483
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
Los Angeles
Meals not included
3 nights + flight
$810
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
8.2 Very good
Near North Side
Free Wi-Fi
Pool
Los Angeles
Meals not included
3 nights + flight
$547
ACME Hotel Chicago, Outset Collection by Hilton - Chicago - Bar
ACME Hotel Chicago, Outset Collection by Hilton - Chicago - Bar
ACME Hotel Chicago, Outset Collection by Hilton
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Spa
Minneapolis St Paul
Meals not included
3 nights + flight
$417
The Drake - Chicago - Lobby
The Drake - Chicago - Lobby
The Drake
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$499
Club Quarters Hotel Wacker at Michigan, Chicago - Chicago - Building
Club Quarters Hotel Wacker at Michigan, Chicago - Chicago - Building
Club Quarters Hotel Wacker at Michigan, Chicago
8.3 Very good
Loop
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$442
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pool
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$953
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
$565

All inclusive vacation 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
All inclusive
3 nights + flight
$878

Last minute vacation packages to Chicago

Show all
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
Newark
Meals not included
3 nights + flight
$975
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
Los Angeles
Breakfast
3 nights + flight
$1,136
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
Los Angeles
Breakfast
3 nights + flight
$877

When to book a vacation in Chicago

Price includes flights and 3 nights accommodation for 2 travelers. Prices are not fixed and may vary with time.

Tips for finding Chicago package deals

  • There are loads of types of vacations 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 travelers: Top vacation $111; Family vacation $308; Romantic vacation $324; Luxury vacation $390; Budget vacation $256.

Where to stay in Chicago

Our map will help you find the perfect place to stay for your vacation in Chicago by showing you the exact location of each hotel.

Everything you need to know for your vacation in Chicago

Chicago vacation information

Top vacation (Flight+Hotel)$111
Family vacation (Flight+Hotel)$308
Romantic vacation (Flight+Hotel)$324
Luxury vacation (Flight+Hotel)$390
Budget vacation (Flight+Hotel)$256