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Sat, Apr 18 - Sun, Apr 19
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$224 Roundtrip, found 12 hours ago
$224
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sat, Apr 18 from Newark Liberty Intl. Airport to Midway Intl., returning Sun, Apr 19, priced at $224 found 12 hours ago
Sat, Apr 18 - Tue, Apr 21
LGA
LaGuardia
MDW
Midway Intl.
$255 Roundtrip, found 11 hours ago
$255
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sat, Apr 18 from LaGuardia to Midway Intl., returning Tue, Apr 21, priced at $255 found 11 hours ago
Sun, Apr 19 - Mon, Apr 20
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$295 Roundtrip, just found
$295
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Apr 19 from Newark Liberty Intl. Airport to O'Hare Intl., returning Mon, Apr 20, priced at $295 just found
Sat, Apr 18 - Mon, Apr 20
LGA
LaGuardia
ORD
O'Hare Intl.
$322 Roundtrip, found 1 hour ago
$322
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Apr 18 from LaGuardia to O'Hare Intl., returning Mon, Apr 20, priced at $322 found 1 hour ago
Sat, May 2 - Sun, May 3
EWR
New York
MDW
Chicago
$56 Roundtrip, found 3 days ago
$56
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, May 2 from New York to Chicago, returning Sun, May 3, priced at $56 found 3 days ago
Wed, Jul 22 - Sat, Jul 25
EWR
New York
ORD
Chicago
$99 Roundtrip, found 9 hours ago
$99
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Wed, Jul 22 from New York to Chicago, returning Sat, Jul 25, priced at $99 found 9 hours ago
Tue, Apr 28 - Wed, May 6
LGA
New York
ORD
Chicago
$106 Roundtrip, found 1 day ago
$106
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Apr 28 from New York to Chicago, returning Wed, May 6, priced at $106 found 1 day ago
Sat, May 2 - Sat, May 9
LGA
New York
MDW
Chicago
$162 Roundtrip, found 5 days ago
$162
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 2 from New York to Chicago, returning Sat, May 9, priced at $162 found 5 days ago
Sat, Apr 25 - Sat, May 2
LGA
New York
MDW
Chicago
$171 Roundtrip, found 4 days ago
$171
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Apr 25 from New York to Chicago, returning Sat, May 2, priced at $171 found 4 days ago
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport
4.0-star property

Hilton Chicago O'Hare Airport

8.4/10 Very Good! (2,241 reviews)

May 23 - May 26

3 night stay

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

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $664, price is now $454 per person
$454
per person
found 1 day ago
This place gets 3 stars from me only due to its great location. It's in rather poor repair and its overall appearance and upkeep do not reflect well on the Hilton brand. It seems clear that property ownership are not bothering to put money into it because they know they will get traffic from the airport.

Reviewed on Feb 25, 2026

Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (436 reviews)

Jun 11 - Jun 15

4 night stay

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

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,030, price is now $713 per person
$713
per person
found 1 day ago
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (453 reviews)

Jun 4 - Jun 8

4 night stay

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

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,638, price is now $1,142 per person
$1,142
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.

Reviewed on Nov 20, 2025

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

Level Chicago Fulton Market

9.2/10 Wonderful! (436 reviews)

May 28 - Jun 4

7 night stay

New York (NYC) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,798, price is now $1,858 per person
$1,858
per person
found 9 hours ago
Eurostars Magnificent Mile
4.0-star property

Eurostars Magnificent Mile

9/10 Wonderful! (3,357 reviews)

May 28 - Jun 4

7 night stay

New York (NYC) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,734, price is now $1,992 per person
$1,992
per person
found 9 hours ago
In convenient area either by walking or uber

Reviewed on Oct 18, 2025

Sports Illustrated Resorts Chicago
3.5-star property

Sports Illustrated Resorts Chicago

9.2/10 Wonderful! (1,409 reviews)

May 28 - Jun 4

7 night stay

New York (NYC) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,150, price is now $2,342 per person
$2,342
per person
found 9 hours ago
The location was great and made it easy to navigate about the city. The staff were all extremely friendly and helpful, and the perks of staying here were great. They offered a complimentary item from the coffee shop and hosted happy hour during my stay. My room was neat and well kept and a great place for me to land.

Reviewed on Jan 20, 2026

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Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
4.0-star property

Eurostars Magnificent Mile

9/10 Wonderful! (3,357 reviews)

Jun 5 - Jun 7

2 night stay

New York (LGA) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,377, price is now $1,076 per person
$1,076
per person
found 1 day ago
In convenient area either by walking or uber

Reviewed on Oct 18, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (3,688 reviews)

Jun 5 - Jun 7

2 night stay

New York (LGA) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,579, price is now $1,204 per person
$1,204
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

Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (2,604 reviews)

Jun 5 - Jun 7

2 night stay

New York (LGA) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,384, price is now $1,124 per person
$1,124
per person
found 1 day ago
The rooms were clean and smelled fresh.

Reviewed on Jan 8, 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.