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Sat, Apr 4 - Mon, Apr 6
LGA
LaGuardia
MDW
Midway Intl.
$250 Roundtrip, found 11 hours ago
$250
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sat, Apr 4 from LaGuardia to Midway Intl., returning Mon, Apr 6, priced at $250 found 11 hours ago
Sat, Apr 4 - Sun, Apr 5
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$251 Roundtrip, found 1 hour ago
$251
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Apr 4 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sun, Apr 5, priced at $251 found 1 hour ago
Sat, Apr 4 - Wed, Apr 8
LGA
LaGuardia
ORD
O'Hare Intl.
$255 Roundtrip, found 1 hour ago
$255
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Apr 4 from LaGuardia to O'Hare Intl., returning Wed, Apr 8, priced at $255 found 1 hour ago
Sat, Apr 4 - Mon, Apr 6
JFK
John F. Kennedy Intl.
MDW
Midway Intl.
$260 Roundtrip, found 7 hours ago
$260
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Apr 4 from John F. Kennedy Intl. to Midway Intl., returning Mon, Apr 6, priced at $260 found 7 hours ago
Wed, Apr 22 - Mon, Apr 27
EWR
New York
MDW
Chicago
$56 Roundtrip, found 11 hours ago
$56
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Wed, Apr 22 from New York to Chicago, returning Mon, Apr 27, priced at $56 found 11 hours ago
Wed, Apr 22 - Wed, Apr 29
LGA
New York
ORD
Chicago
$87 Roundtrip, found 8 hours ago
$87
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Wed, Apr 22 from New York to Chicago, returning Wed, Apr 29, priced at $87 found 8 hours ago
Mon, Apr 13 - Sat, Apr 18
EWR
New York
ORD
Chicago
$99 Roundtrip, found 2 days ago
$99
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Mon, Apr 13 from New York to Chicago, returning Sat, Apr 18, priced at $99 found 2 days ago
Sat, May 2 - Tue, May 5
LGA
New York
MDW
Chicago
$142 Roundtrip, found 10 hours ago
$142
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sat, May 2 from New York to Chicago, returning Tue, May 5, priced at $142 found 10 hours ago
Sun, May 10 - Thu, May 21
LGA
New York
ORD
Chicago
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, May 10 from New York to Chicago, returning Thu, May 21, priced at $177 found 2 days ago
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (2,582 reviews)

May 16 - May 19

3 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $955, price is now $707 per person
$707
per person
found 1 day ago
The rooms were clean and smelled fresh.

Reviewed on Jan 8, 2026

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (3,495 reviews)

May 16 - May 19

3 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,313, price is now $895 per person
$895
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,401 reviews)

May 29 - Jun 1

3 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,809, price is now $1,280 per person
$1,280
per person
found 10 hours ago
Courteous staff, clean room, conveniently located right on the pier.

Reviewed on Nov 3, 2025

Don't see what you're looking for?
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Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Midway
3.5-star property

Chicago Marriott Midway

8.4/10 Very Good! (924 reviews)

May 15 - May 17

2 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $783, price is now $731 per person
$731
per person
found 7 hours ago
The health club was excellent. I didn't like the Internet service at 9.95 daily.

Reviewed on Aug 20, 2025

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
4.0-star property

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

8/10 Very Good! (1,013 reviews)

May 15 - May 17

2 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $781, price is now $732 per person
$732
per person
found 7 hours ago
Nice Hotel. Reasonable Price. Room was clean. Property could use updating.

Reviewed on Aug 5, 2025

Courtyard by Marriott Chicago Midway Airport
3.0-star property

Courtyard by Marriott Chicago Midway Airport

8.2/10 Very Good! (1,005 reviews)

May 15 - May 17

2 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $794, price is now $744 per person
$744
per person
found 7 hours ago
Staff was excellent as always although they not responsible for the power outage Tuesday night that lasted approximately 7 hours. Sadly I will complain and seek credit for the inconvenience.

Reviewed on Jan 7, 2026

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.