Vacations in Chicago

Vacations in Chicago

2 travelers

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Cheap Chicago package deals

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$145 - $381$381 - $618$618 - $854$854 - $1,090$1,090+ per night

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Most popular Chicago flight and hotel deals

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The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
8.1 Very good
Near North Side
Pool
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$246
Intercontinental Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Chicago Magnificent Mile By IHG
8 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$379
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
8.2 Very good
Near North Side
New York John F Kennedy Intl
Meals not included
3 nights + flight
$155
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.5 Very good
Near North Side
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$215
Kimpton Gray Hotel - Chicago - Lobby
Kimpton Gray Hotel - Chicago - Lobby
Kimpton Gray Hotel
8.9 Very good
Downtown
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
$458
21c Museum Hotel Chicago - Chicago - Restaurant
21c Museum Hotel Chicago - Chicago - Restaurant
21c Museum Hotel Chicago
8.4 Very good
Near North Side
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$313
Hampton Inn & Suites Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites Chicago Medical District UIC
9.1 Wonderful
Near West Side
Pool
Pet friendly
Philadelphia
Breakfast
3 nights + flight
$287
Palmer House a Hilton Hotel - Chicago - Lobby
Palmer House a Hilton Hotel - Chicago - Lobby
Palmer House a Hilton Hotel
7.8 Good
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Philadelphia
Meals not included
3 nights + flight
$307
Hampton Inn & Suites Chicago-Downtown - Chicago - Lobby
Hampton Inn & Suites Chicago-Downtown - Chicago - Lobby
Hampton Inn & Suites Chicago-Downtown
8.6 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Nashville Intl
Breakfast
3 nights + flight
$298
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago
9 Wonderful
Near North Side
Pool
Pet friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$930
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room
The Allegro Royal Sonesta Hotel Chicago Loop
8.3 Very good
Downtown
Pet friendly
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$286
DoubleTree by Hilton Chicago Magnificent Mile - Chicago - Lounge
DoubleTree by Hilton Chicago Magnificent Mile - Chicago - Lounge
DoubleTree by Hilton Chicago Magnificent Mile
7.9 Good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$252
Claridge House - Chicago - Lobby
Claridge House - Chicago - Lobby
Claridge House
8 Very good
Near North Side
Free Wi-Fi
Pet friendly
Spa
Philadelphia
Meals not included
3 nights + flight
$266
Sofitel Chicago Magnificent Mile - Chicago - Patio
Sofitel Chicago Magnificent Mile - Chicago - Patio
Sofitel Chicago Magnificent Mile
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
$346
Hampton Inn Chicago Downtown/Magnificent Mile - Chicago - Living room
Hampton Inn Chicago Downtown/Magnificent Mile - Chicago - Living room
Hampton Inn Chicago Downtown/Magnificent Mile
7.6 Good
Near North Side
Free Wi-Fi
Pet friendly
Philadelphia
Breakfast
3 nights + flight
$276
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
Pet friendly
Spa
Tampa
Meals not included
3 nights + flight
$944

All inclusive vacation packages to Chicago

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The Wheeler Mansion - Chicago - Dining room
The Wheeler Mansion - Chicago - Dining room
The Wheeler Mansion
9.8 Wonderful
Near South Side
Free Wi-Fi
Phoenix Sky Harbor Intl
All inclusive
3 nights + flight
$817

Last minute vacation packages to Chicago

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Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical - Chicago - Lounge
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical - Chicago - Lounge
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
8.1 Very good
Near North Side
Free Wi-Fi
Pet friendly
Orlando
Breakfast
3 nights + flight
$565

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 $312; Family vacation $302; Romantic vacation $332; Luxury vacation $320; Budget vacation $237.

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)$312
Family vacation (Flight+Hotel)$302
Romantic vacation (Flight+Hotel)$332
Luxury vacation (Flight+Hotel)$320
Budget vacation (Flight+Hotel)$237

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