Holidays in Chicago

Holidays in Chicago

2 travellers
Exact dates

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

Here is why travellers 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 30 Apr - 3 May.
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

€170 - €332€332 - €495€495 - €657€657 - €820€820+ per night

Search by freebies

Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

Show all
River Hotel - Chicago - Lobby
River Hotel - Chicago - Lobby
River Hotel
8.4 Very Good
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Raleigh-Durham
Meals not included
3 nights + flight
€295
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown
8.3 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€373
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€688
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€516
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
Downtown
Free Wi-Fi
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€415
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€326
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop
8.3 Very Good
Downtown
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Miami
Meals not included
3 nights + flight
€394
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
8.8 Very Good
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Denver Intl
Breakfast
3 nights + flight
€440
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
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€388
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago
9.2 Wonderful
Near North Side
Pool
Pet friendly
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€661
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.2 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€561
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk
8.4 Very Good
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Miami
Meals not included
3 nights + flight
€317
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel
8.7 Very Good
Downtown
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€569
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.6 Very Good
Downtown
Free Wi-Fi
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€424
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.6 Very Good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€688
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection
8.6 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€425

All inclusive holiday 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
Air conditioning
Denver Intl
All-inclusive
3 nights + flight
€716

Last minute holiday 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
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€373
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.3 Very Good
Near North Side
Free Wi-Fi
Pool
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€329
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.7 Very Good
Near West Side
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Breakfast
3 nights + flight
€370

When to book a holiday in Chicago

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

Tips for finding Chicago package deals

  • There are loads of types of holidays 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 travellers: Top holiday €127; Family holiday €508; Romantic holiday €508; Budget holiday €508.

Where to stay in Chicago

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

Everything you need to know for your holiday in Chicago

Chicago holiday information

Top holiday (Flight+Hotel)€127
Family holiday (Flight+Hotel)€508
Romantic holiday (Flight+Hotel)€508
Budget holiday (Flight+Hotel)€508