Vacations in Chicago

Vacations in Chicago

2 travelers

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Cheap Chicago package deals

These are the best prices for Sep 20 - 23.
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$230 - $375$375 - $519$519 - $664$664 - $808$808+ 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
7.9 Good
Near North Side
Pool
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$471
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
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$350
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
8.2 Very good
Near North Side
Free Wi-Fi
Pet friendly
Tampa
Breakfast
3 nights + flight
$406
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
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$389
Hyatt Centric Chicago Magnificent Mile - Chicago - Bar
Hyatt Centric Chicago Magnificent Mile - Chicago - Bar
Hyatt Centric Chicago Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$482
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Orlando
Meals not included
3 nights + flight
$638
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
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$460
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Tampa
Meals not included
3 nights + flight
$407
Hyatt Regency Chicago - Chicago - Bedroom
Hyatt Regency Chicago - Chicago - Bedroom
Hyatt Regency Chicago
8.7 Very good
Downtown
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$521
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
San Francisco
Meals not included
3 nights + flight
$664
Best Western River North Hotel - Chicago - Balcony
Best Western River North Hotel - Chicago - Balcony
Best Western River North Hotel
7.3 Good
Near North Side
Free Wi-Fi
Pool
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$382
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.5 Very good
Downtown
Free Wi-Fi
Tampa
Meals not included
3 nights + flight
$445
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.6 Very good
Downtown
Free Wi-Fi
Pet friendly
Tampa
Meals not included
3 nights + flight
$434
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.2 Good
Downtown
Free Wi-Fi
Newark
Meals not included
3 nights + flight
$420
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
Orlando
Meals not included
3 nights + flight
$478
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
Downtown
Free Wi-Fi
Pet friendly
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$418

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
Tampa
All inclusive
3 nights + flight
$576

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
Downtown
Pet friendly
San Francisco
Meals not included
3 nights + flight
$530

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