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 13-16 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

€222 - €384€384 - €546€546 - €708€708 - €870€870+ per night

Search by freebies

Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

Show all
Thompson Chicago - Chicago - Living room
Thompson Chicago - Chicago - Living room
Thompson Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
€413
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet friendly
Air conditioning
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
€427
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.6 Very Good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Fort Lauderdale
Half board
3 nights + flight
€309
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
Air conditioning
Charlotte Douglas
Breakfast
3 nights + flight
€333
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
7.9 Good
Near North Side
Pool
Pet friendly
Air conditioning
Charlotte Douglas
Breakfast
3 nights + flight
€362
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
Fort Lauderdale
Breakfast
3 nights + flight
€384
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Charlotte Douglas
Meals not included
3 nights + flight
€508
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
Charlotte Douglas
Meals not included
3 nights + flight
€356
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
Charlotte Douglas
Meals not included
3 nights + flight
€370
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop
8.9 Very Good
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Charlotte Douglas
Meals not included
3 nights + flight
€365
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
Charlotte Douglas
Meals not included
3 nights + flight
€347
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
Charlotte Douglas
Meals not included
3 nights + flight
€342
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
Fort Lauderdale
Meals not included
3 nights + flight
€627
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
Charlotte Douglas
Meals not included
3 nights + flight
€396
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
Charlotte Douglas
Meals not included
3 nights + flight
€399
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
Charlotte Douglas
Meals not included
3 nights + flight
€372

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
Raleigh-Durham
All-inclusive
3 nights + flight
€749

Last minute holiday packages to Chicago

Show all
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
South Side
Free Wi-Fi
Air conditioning
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
€610

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 €128; Family holiday €511; Romantic holiday €511; Budget holiday €511.

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)€128
Family holiday (Flight+Hotel)€511
Romantic holiday (Flight+Hotel)€511
Budget holiday (Flight+Hotel)€511