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Princeton Vacation Packages

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Princeton Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Save 100% on your flight
Price was $659, price is now $349 per person
$349
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Price was $4,740, price is now $2,744 per person
$2,744
per person
Sep 13 - Sep 19
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.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $997, price is now $619 per person
$619
per person
Oct 18 - Oct 21
found 1 day 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.

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 $1,452, price is now $904 per person
$904
per person
Oct 8 - Oct 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, 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.
Great beautiful rooms. Nice beds

Reviewed on Aug 7, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $755, price is now $472 per person
$472
per person
Oct 15 - Oct 18
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.
I truly enjoyed my stay! It was a great experience and definitely worth the visit. I loved the fact that all of my activities were all in proximity of the hotel. 10/10

Reviewed on Aug 7, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,235, price is now $797 per person
$797
per person
Sep 10 - Sep 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.

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $717, price is now $472 per person
$472
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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.
This place showed up in the options for 18+ check-in allowed, but it turns out it wasn't. That might be my fault on my part but it should be made clearer through Expedia. Staff were okay; some were a little rude but not overly. The hotel room itself was clean, and there were no problems in that regard. The stay was expensive due to travelling during Lollapalooza and would most likely be cheaper at any other time. Overall 3/5. Not worth the money, but would be much more worth it if it was cheaper.

Reviewed on Aug 6, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,566, price is now $1,042 per person
$1,042
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
Worst hotel stay in Chicago.

Reviewed on Aug 6, 2026

Princeton Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Downtown Chicago
Save 100% on your flight
Price was $659, price is now $349 per person
$349
per person
Oct 15 - Oct 18
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 $1,624, price is now $974 per person
$974
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $997, price is now $619 per person
$619
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,452, price is now $904 per person
$904
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Princeton Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,668, price is now $1,037 per person
$1,037
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,255, price is now $1,220 per person
$1,220
per person
Oct 19 - Oct 26
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was $4,740, price is now $2,744 per person
$2,744
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,450, price is now $1,514 per person
$1,514
per person
Sep 13 - Sep 19
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, Aug 29 - Sat, Sep 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$171 Roundtrip, just found
$171
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Aug 29 from Los Angeles Intl. to O'Hare Intl., returning Sat, Sep 5, priced at $171 just found
American Airlines
Wed, Nov 4 - Wed, Nov 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 6 hours ago
$197
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, Nov 4 from Los Angeles Intl. to O'Hare Intl., returning Wed, Nov 11, priced at $197 found 6 hours ago
United
Wed, Nov 4 - Wed, Nov 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 6 hours ago
$197
Roundtrip
found 6 hours ago
Select United flight, departing Wed, Nov 4 from Los Angeles Intl. to O'Hare Intl., returning Wed, Nov 11, priced at $197 found 6 hours ago
Hainan Airlines
Tue, Sep 1 - Fri, Sep 18
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,131 Roundtrip, found 3 days ago
$1,131
Roundtrip
found 3 days ago
Select Hainan Airlines flight, departing Tue, Sep 1 from Capital Intl. to O'Hare Intl., returning Fri, Sep 18, priced at $1,131 found 3 days ago