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Vacations in Chicago

Vacations in Chicago

2 travelers

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$261 - $440$440 - $619$619 - $798$798 - $977$977+ per night

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Most popular Chicago flight and hotel deals

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River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.3 Very good
Loop
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
$305
Residence Inn by Marriott Chicago Downtown/River North - Chicago - Building
Residence Inn by Marriott Chicago Downtown/River North - Chicago - Building
Residence Inn by Marriott Chicago Downtown/River North
8.5 Very good
Near North Side
Free Wi-Fi
Pet friendly
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$473
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel - Chicago - Restaurant
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel - Chicago - Restaurant
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
$373
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection
7.8 Good
Near North Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
$271
FOUND Hotels, Chicago, Series by Marriott - Chicago - Bedroom
FOUND Hotels, Chicago, Series by Marriott - Chicago - Bedroom
FOUND Hotels, Chicago, Series by Marriott
7.8 Good
Near North Side
Free Wi-Fi
Baltimore/Washington
Meals not included
3 nights + flight
$327
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop
8.6 Very good
Loop
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Breakfast
3 nights + flight
$437
Hotel Felix - Chicago - Lobby
Hotel Felix - Chicago - Lobby
Hotel Felix
7.6 Good
Near North Side
Free Wi-Fi
Pet friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$328
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Building
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Building
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
$408
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago
8.2 Very good
Near North Side
Pet friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$438
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Building
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Building
SpringHill Suites by Marriott Chicago Downtown/River North
8.8 Very good
Near North Side
Free Wi-Fi
Baltimore/Washington
Breakfast
3 nights + flight
$454
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago - Chicago - Bar
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago - Chicago - Bar
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
9 Wonderful
Near North Side
Pet friendly
Miami
Meals not included
3 nights + flight
$729
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel
8.1 Very good
Loop
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
$300
Sofitel Chicago Magnificent Mile - Chicago - Lobby
Sofitel Chicago Magnificent Mile - Chicago - Lobby
Sofitel Chicago Magnificent Mile
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
$516
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
Baltimore/Washington
Meals not included
3 nights + flight
$307
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
Orlando
Meals not included
3 nights + flight
$432
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
Baltimore/Washington
Meals not included
3 nights + flight
$319

Last minute vacation packages to Chicago

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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
Ontario
Meals not included
3 nights + flight
$855
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
7.9 Good
Near North Side
Free Wi-Fi
Pet friendly
Ontario
Breakfast
3 nights + flight
$640
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.9 Very good
Near West Side
Free Wi-Fi
Pet friendly
Ontario
Meals not included
3 nights + flight
$661
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Meeting room
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Meeting room
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
Chinatown
Free Wi-Fi
Philadelphia
Breakfast
3 nights + flight
$1,012

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 $116; Family vacation $278; Romantic vacation $324; Luxury vacation $426; Budget vacation $251.

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)$116
Family vacation (Flight+Hotel)$278
Romantic vacation (Flight+Hotel)$324
Luxury vacation (Flight+Hotel)$426
Budget vacation (Flight+Hotel)$251