Vacations Close To Lakefront Trail

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Lakefront Trail Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $730, price is now $541 per person
$541
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,255, price is now $818 per person
$818
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $1,834, price is now $1,203 per person
$1,203
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
This is an elegant and high class facility with warm service and hospitality stuff Centrally located on North River north bank. The room is big and spacious overlooking the river. We loved our stay. The concierge gave us a great tips and services Recommend by all means.

Reviewed on Oct 2, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,006, price is now $711 per person
$711
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,384, price is now $1,013 per person
$1,013
per person
Nov 5 - Nov 10
found 13 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was $858, price is now $632 per person
$632
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,374, price is now $1,016 per person
$1,016
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Fantastic as always. Highly recommend

Reviewed on Oct 1, 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was $893, price is now $667 per person
$667
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Great hotel with great staff in a good location. Would use again.

Reviewed on Oct 1, 2026

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Best Lodging Options Near Lakefront Trail

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
3.77 km from Lakefront Trail
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
1.24 km from Lakefront Trail
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
5.14 km from Lakefront Trail
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
3.5 km from Lakefront Trail
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Marriott Marquis Chicago

Marriott Marquis Chicago

4 out of 5
2121 South Prairie Avenue Chicago IL
1.53 km from Lakefront Trail
Book a stay at this business-friendly hotel in Chicago. Enjoy 9 restaurants, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
Hilton Garden Inn Chicago McCormick Place

Hilton Garden Inn Chicago McCormick Place

3 out of 5
123 East Cermak, Suite 300 Chicago IL
1.57 km from Lakefront Trail
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. ...
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd Chicago IL
2.35 km from Lakefront Trail
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
172 W Adams St Chicago IL
4.51 km from Lakefront Trail
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the ...
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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.