Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Price was $623, price is now $457 per person
$457
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Rosemont Theatre are located nearby.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,868, price is now $1,238 per person
$1,238
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
Save 100% on your flight
Price was $847, price is now $565 per person
$565
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.
I don’t know if I would pay the extra money to stay here unless we planned to go to the casino.
It was a lot of extra trouble getting into the hotel with all our baggage!
Reviewed on Oct 3, 2026
Level Chicago Fulton Market
Price was $857, price is now $607 per person
$607
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Stay One Chicago
Save 100% on your flight
Price was $1,088, price is now $782 per person
$782
per person
Dec 19 - Dec 22
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, private pools, and 3 restaurants. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The instructions on how to access the room were excellent and the room was well maintained and well stocked. Excellent choice for the price and location.
Reviewed on Oct 2, 2026
Hotel Riu Plaza Chicago
Price was $1,542, price is now $1,111 per person
$1,111
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Great hotel
Reviewed on Oct 4, 2026
Four Seasons Hotel Chicago
Save 100% on your flight
Price was $1,966, price is now $1,435 per person
$1,435
per person
Dec 22 - Dec 27
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hyatt Centric Chicago Magnificent Mile
Save 100% on your flight
Price was $868, price is now $635 per person
$635
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Excellent hotel! The location is cute and definitely a boutique hotel. We have older teens so it worked for us. Not ideal for younger kinds. Very well maintained.
Clean
Great housekeeping
Friendly staff
Bougie
Reviewed on Oct 3, 2026
Chicago Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chicago Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$119 Roundtrip, just found
$119
Roundtrip
just found
Tue, Nov 17 - Thu, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$156 Roundtrip, found 11 hours ago
$156
Roundtrip
found 11 hours ago
Wed, Oct 21 - Thu, Nov 5
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$176 Roundtrip, found 3 days ago
$176
Roundtrip
found 3 days ago
Wed, Nov 18 - Wed, Nov 18
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
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