Search Deals onOakbrook Terrace Vacation Packages
Oakbrook Terrace Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Save 100% on your flight
Price was $726, price is now $488 per person
$488
per person
Nov 6 - Nov 8
found 1 day 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 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market
Save 100% on your flight
Price was $1,059, price is now $604 per person
$604
per person
Oct 29 - Nov 2
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.
👍
Reviewed on Sep 28, 2026
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,086, price is now $646 per person
$646
per person
Nov 6 - Nov 8
found 1 day 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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Trump hotel is right in the middle of downtown, but it's on the quieter side of the river from the other hotels. It offers direct access to the river where you can join the architecture river tour and is overall quieter than the hotels on the other side of the river. The self parking is a bit of a tricky drive up very narrow and curving ramps. If you drive a Suburban or a Cybertruck, you might have difficulty.
Reviewed on Sep 29, 2026
Level Chicago – Old Town
Save 100% on your flight
Price was $1,211, price is now $741 per person
$741
per person
Oct 29 - Nov 2
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.
Reviewed on Sep 27, 2026
The Peninsula Chicago
Save 100% on your flight
Price was $1,816, price is now $1,165 per person
$1,165
per person
Nov 22 - Nov 26
found 24 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 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
It is the greatest will be there again
Reviewed on Sep 29, 2026
Thompson Chicago, by Hyatt
Save 100% on your flight
Price was $943, price is now $650 per person
$650
per person
Nov 20 - Nov 23
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 bars/lounges, 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.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $717, price is now $495 per person
$495
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Le Méridien Essex Chicago
Save 100% on your flight
Price was $790, price is now $548 per person
$548
per person
Nov 30 - Dec 2
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, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Would not eat the bar restaurant. Messed up our order as well as others around us
Reviewed on Sep 29, 2026
Oakbrook Terrace Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Oakbrook Terrace 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.
Mon, Nov 9 - Fri, Nov 13
LAX
Los Angeles Intl.
MDW
Midway Intl.
$200 Roundtrip, found 15 hours ago
$200
Roundtrip
found 15 hours ago
Wed, Nov 4 - Tue, Nov 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$200 Roundtrip, found 21 hours ago
$200
Roundtrip
found 21 hours ago
Wed, Nov 4 - Tue, Nov 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$200 Roundtrip, found 21 hours ago
$200
Roundtrip
found 21 hours ago
Fri, Nov 13 - Fri, Nov 27
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,072 Roundtrip, just found
$1,072
Roundtrip
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