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 Jul 31 - Aug 3.
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

$180 - $345$345 - $509$509 - $674$674 - $838$838+ per night

Search by freebies

Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

Show all
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Hotels Chicago Magnificent Mile By IHG
8.1 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Washington, D.C. Dulles Intl
Meals not included
3 nights + flight
$526
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
7.9 Good
Near North Side
Free Wi-Fi
Pet friendly
Nashville Intl
Breakfast
3 nights + flight
$507
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel - Chicago - Restaurant
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel - Chicago - Restaurant
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
8 Very good
Loop
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
$480
The Chicago Hotel Collection Ambassador Gold Coast - Chicago - Lounge
The Chicago Hotel Collection Ambassador Gold Coast - Chicago - Lounge
The Chicago Hotel Collection Ambassador Gold Coast
8.1 Very good
Near North Side
Tampa
Meals not included
3 nights + flight
$477
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
2.8 Poor
Chatham
Parking
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
$262
City Suites Hotel - Chicago - Bedroom
City Suites Hotel - Chicago - Bedroom
City Suites Hotel
8.3 Very good
Lake View
Free Wi-Fi
Tampa
Meals not included
3 nights + flight
$526
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.4 Very good
Loop
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
$521
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
8.9 Very good
Loop
Free Wi-Fi
Spa
Tampa
Meals not included
3 nights + flight
$551
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Baltimore/Washington
Meals not included
3 nights + flight
$558
Aloft Chicago Mag Mile - Chicago - Pool
Aloft Chicago Mag Mile - Chicago - Pool
Aloft Chicago Mag Mile
8.2 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Tampa
Meals not included
3 nights + flight
$495
The Langham Chicago - Chicago - Lounge
The Langham Chicago - Chicago - Lounge
The Langham Chicago
9.4 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Tampa
Meals not included
3 nights + flight
$708
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
Tampa
Meals not included
3 nights + flight
$652
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
Pet friendly
Spa
Tampa
Meals not included
3 nights + flight
$765
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
Tampa
Meals not included
3 nights + flight
$481
Club Quarters Hotel Central Loop, Chicago - Chicago - Lobby
Club Quarters Hotel Central Loop, Chicago - Chicago - Lobby
Club Quarters Hotel Central Loop, Chicago
8.2 Very good
Loop
Free Wi-Fi
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
$424
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection
8.5 Very good
Near North Side
Free Wi-Fi
Pet friendly
Tampa
Meals not included
3 nights + flight
$513

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
Seattle/Tacoma Intl
All inclusive
3 nights + flight
$614

Last minute vacation packages to Chicago

Show all
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
7.9 Good
Loop
Pool
Pet friendly
Spa
Tampa
Meals not included
3 nights + flight
$838
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
Tampa
Meals not included
3 nights + flight
$509
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare
7.5 Good
O'Hare - International
Airport shuttle
Free Wi-Fi
Pool
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$524

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