Cheap Vacations in Chicago
- Chicago vacations
- 3-night Chicago vacations
- 4-night Chicago vacations
- 5-night Chicago vacations
- 6-7 night Chicago vacations
Chicago vacations
Price found within the past 48 hours. Click for updated prices.
3-night Chicago vacations
Price found within the past 48 hours. Click for updated prices.
4-night Chicago vacations
Price found within the past 48 hours. Click for updated prices.
5-night Chicago vacations
Price found within the past 48 hours. Click for updated prices.
6-7 night Chicago vacations
Price found within the past 48 hours. Click for updated prices.
Flight deals to Chicago
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
ATL
Atlanta
MDW
Chicago
$123 Roundtrip, found 21 hours ago
$123
Roundtrip
found 21 hours ago
ATL
Atlanta
ORD
Chicago
$123 Roundtrip, found 21 hours ago
$123
Roundtrip
found 21 hours ago
DFW
Dallas
ORD
Chicago
$147 Roundtrip, found 21 hours ago
$147
Roundtrip
found 21 hours ago
Top rated hotels for your Chicago vacation
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$136 nightly
The price is $162 total per night
$162 total
Jun 29 - Jun 30
Total with taxes and fees
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Free WiFi
Restaurant
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.35 mi from city center
$139 nightly
The price is $166 total per night
$166 total
Jul 1 - Jul 2
Total with taxes and fees
With a stay at Hilton Chicago/Magnificent Mile Suites, you'll be centrally located in Chicago, steps from Michigan Avenue and 8 minutes by foot from Lake Michigan.
Pool
Pet friendly
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Free Cancellation
Reserve now, pay when you stay
13.75 mi from city center
$127 nightly
The price is $145 total per night
$145 total
Jul 2 - Jul 3
Total with taxes and fees
With a stay at Hyatt Regency O'Hare Chicago in Rosemont, you'll be connected to the convention center, a 5-minute walk from Donald E. Stephens Convention Center and a 5-minute drive from Allstate Arena.
Free airport shuttle
Pet friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Picks
- Romantic Getaways & Hotels in The Loop
- Chicago Hotels
- Hotels near Navy Pier
- 5 Star Hotels in Downtown Chicago
- Hyatt Hotels in Chicago
- Hotels near Art Institute of Chicago
- Hotels with a Wedding Venue in Magnificent Mile
- Hotels near Millennium Park
- Cheap Hotels in The Loop
- Hotels with Kitchenettes in River North
- Hotels with WiFi in The Loop
- Flights from Guangzhou to Chicago
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- Flights from Providenciales to Chicago
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- Schaumburg Vacations
- Field Museum of Natural History
- Adler Planetarium and Astronomy Museum
- Glenview Vacations
- Museum of Contemporary Art Chicago
- Glencoe Vacations
- Wrigley Field
- Legoland® Discovery Center
- Lincolnshire Vacations
- Schiller Park Vacations
- Thornton Junction Vacations
- Tribune Tower
- Hyde Park Vacations
- Magnificent Mile Vacations
- Cloud Gate
- Allstate Arena
- Oakbrook Terrace Vacations
- Goodman Theater
- Addison Vacations
- Navy Pier
- Chicago Cultural Center
- Donald E. Stephens Convention Center
- Wood Dale Vacations
- Pilsen Vacations
- Mccormick Place
- Bridgeview Vacations
- Skokie Vacations
- Aragon Ballroom
- Griffin Museum of Science and Industry
- Montrose Beach
^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.
