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Cicero Vacation Packages

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Cicero Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,265, price is now $799 per person
$799
per person
Nov 3 - Nov 6
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.

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Save 100% on your flight
Price was $1,954, price is now $1,141 per person
$1,141
per person
Nov 5 - 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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The staff was so kind and helpful. Great location and dining options. The room was spotless and comfortable

Reviewed on Aug 30, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,713, price is now $1,082 per person
$1,082
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
We stayed here for 4 nights visiting for the BTS concert. With it being around the time of a big event like that, the prices for hotels were crazy and this was what we could afford at the time and this place was really nice for what we paid. Only complaint is the rooms are a bit small but the bed was big & nice, bathroom and shower was decent size. Also, wish there was better lighting in the room. The free water in the lobby was nice and the free fruit and coffee in the morning was great. Staff was very kind. It’s in a convenient location to bus stops and red line station so it was easy for us to get where we needed to go. Overall very happy with our stay.

Reviewed on Aug 30, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $2,658, price is now $1,688 per person
$1,688
per person
Oct 9 - Oct 13
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.
It was an incredible time in Hotel Riu Plaza Chicago. We will surely stay there again on our next visit to the city. Everything was amazing. Thank you so much.

Reviewed on Aug 30, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,650, price is now $1,081 per person
$1,081
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
Price was $4,335, price is now $2,925 per person
$2,925
per person
Nov 3 - Nov 10
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 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The service and the staff iare incredible, do professional!! So many details! My husband and I were so happy!!

Reviewed on Aug 25, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $1,504, price is now $1,029 per person
$1,029
per person
Nov 3 - Nov 8
found 20 hours ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,823, price is now $1,260 per person
$1,260
per person
Nov 3 - Nov 8
found 20 hours ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.

Cicero Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,265, price is now $799 per person
$799
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,954, price is now $1,141 per person
$1,141
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,713, price is now $1,082 per person
$1,082
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,658, price is now $1,688 per person
$1,688
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Cicero Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,921, price is now $1,128 per person
$1,128
per person
Oct 15 - Oct 20
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,227, price is now $1,197 per person
$1,197
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,940, price is now $1,660 per person
$1,660
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,928, price is now $1,154 per person
$1,154
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 3 hours ago
$138
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Oct 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $138 found 3 hours ago
Southwest Airlines
Tue, Sep 22 - Tue, Sep 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$241 Roundtrip, found 17 hours ago
$241
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Tue, Sep 22 from Los Angeles Intl. to Midway Intl., returning Tue, Sep 29, priced at $241 found 17 hours ago
American Airlines
Wed, Sep 2 - Wed, Sep 16
LAX
Los Angeles Intl.
RFD
Greater Rockford
$300 Roundtrip, found 3 days ago
$300
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Sep 2 from Los Angeles Intl. to Greater Rockford, returning Wed, Sep 16, priced at $300 found 3 days ago
Air China
Sat, Sep 5 - Wed, Sep 16
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,184 Roundtrip, found 5 hours ago
$1,184
Roundtrip
found 5 hours ago
Select Air China flight, departing Sat, Sep 5 from Capital Intl. to O'Hare Intl., returning Wed, Sep 16, priced at $1,184 found 5 hours ago