$105 Cheap flight deals from Chicago (CHI) to Brentwood (BNA)

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This Weekend's Flight Deals from Chicago to Brentwood

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Jun 21 - Fri, Jul 3
ORD
O'Hare Intl.
BNA
Nashville Intl.
$385 Roundtrip, found 2 hours ago
$385
Roundtrip
found 2 hours ago
Select Contour Airlines flight, departing Sun, Jun 21 from O'Hare Intl. to Nashville Intl., returning Fri, Jul 3, priced at $385 found 2 hours ago
Sat, Jun 20 - Sat, Jun 20
MDW
Midway Intl.
BNA
Nashville Intl.
$411 Roundtrip, found 1 day ago
$411
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Jun 20 from Midway Intl. to Nashville Intl., returning Sat, Jun 20, priced at $411 found 1 day ago
Sun, Jun 21 - Mon, Jun 22
RFD
Greater Rockford
BNA
Nashville Intl.
$729 Roundtrip, found 6 hours ago
$729
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sun, Jun 21 from Greater Rockford to Nashville Intl., returning Mon, Jun 22, priced at $729 found 6 hours ago

Airfares from $105 One Way, $210 Round Trip from Chicago to Brentwood

Prices starting at $210 for return flights and $105 for one-way flights to Brentwood were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Aug 18 - Tue, Aug 25
ORD
Chicago
BNA
Nashville
$210 Roundtrip, found 13 hours ago
$210
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Chicago to Nashville, returning Tue, Aug 25, priced at $210 found 13 hours ago
Wed, Aug 5 - Thu, Aug 6
ORD
Chicago
BNA
Nashville
$214 Roundtrip, found 6 days ago
$214
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Aug 5 from Chicago to Nashville, returning Thu, Aug 6, priced at $214 found 6 days ago
Thu, Sep 10 - Sun, Sep 13
ORD
Chicago
BNA
Nashville
$229 Roundtrip, just found
$229
Roundtrip
just found
Select Contour Airlines flight, departing Thu, Sep 10 from Chicago to Nashville, returning Sun, Sep 13, priced at $229 just found
Wed, Aug 5 - Thu, Aug 6
ORD
Chicago
BNA
Nashville
$234 Roundtrip, found 6 days ago
$234
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Aug 5 from Chicago to Nashville, returning Thu, Aug 6, priced at $234 found 6 days ago
Tue, Aug 18 - Tue, Aug 25
MDW
Chicago
BNA
Nashville
$259 Roundtrip, found 13 hours ago
$259
Roundtrip
found 13 hours ago
Select Southwest Airlines flight, departing Tue, Aug 18 from Chicago to Nashville, returning Tue, Aug 25, priced at $259 found 13 hours ago

Brentwood economy flight packages

Price found within the past 48 hours. Click for updated prices.
Fairlane Hotel
4.0-star property

Fairlane Hotel

9.4/10 Exceptional! (1,003 reviews)

Aug 7 - Aug 9

2 night stay

Chicago (CHI) to Nashville (BNA)

Contour Airlines • Non-stop • Coach

Nashville (BNA) to Chicago (CHI)

Frontier Airlines • Non-stop • Coach
Price was $575, price is now $411 per person
$411
per person
found 1 day ago
Loves this property. The staff was absolutely amazing and sooo helpful. I was not interested in the resturants so we did not eat them. It was close to everything downtown and we walked everywhere. Felt safe when walking. I loved the shower in the room! My only complaint would be that they don't have the ability to log into streaming services and that would prevent me from staying again. There wasnt even the ability to screen share.

Reviewed on Mar 22, 2026

Harthall Hotel
4.0-star property

Harthall Hotel

8.4/10 Very Good! (108 reviews)

Aug 10 - Aug 13

3 night stay

Chicago (CHI) to Nashville (BNA)

Southwest Airlines • Coach

Nashville (BNA) to Chicago (CHI)

Frontier Airlines • Coach
Price was $693, price is now $456 per person
$456
per person
found 1 day ago
Conrad Nashville
5.0-star property

Conrad Nashville

9.6/10 Exceptional! (1,082 reviews)

Jul 23 - Jul 27

4 night stay

Chicago (CHI) to Nashville (BNA)

Contour Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,399, price is now $967 per person
$967
per person
found 1 day ago
Shower was broken and hair dryer was broken. Make up mirror didn't work either. Draperies are controlled by a switch that was hard to read because the letters were the same color as the background.

Reviewed on Oct 8, 2025

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Brentwood first class flight packages

Price found within the past 48 hours. Click for updated prices.
Kimpton Aertson Hotel by IHG
4.5-star property

Kimpton Aertson Hotel by IHG

9.2/10 Wonderful! (1,005 reviews)

Jul 18 - Jul 22

4 night stay

Chicago (ORD) to Nashville (BNA)

American Airlines • Roundtrip • FirstClass
Price was $1,118, price is now $901 per person
$901
per person
found 22 hours ago
Great hotel right next to Vanderbilt and a walkable area with live music.

Reviewed on Sep 8, 2025

1 Hotel Nashville
5.0-star property

1 Hotel Nashville

9.4/10 Exceptional! (1,010 reviews)

Jul 18 - Jul 22

4 night stay

Chicago (ORD) to Nashville (BNA)

American Airlines • Roundtrip • FirstClass
Price was $1,750, price is now $1,276 per person
$1,276
per person
found 22 hours ago
Lovely rooms, friendly staff, spa like experience.

Reviewed on Oct 20, 2024

Fairlane Hotel
4.0-star property

Fairlane Hotel

9.4/10 Exceptional! (1,003 reviews)

Jul 18 - Jul 22

4 night stay

Chicago (ORD) to Nashville (BNA)

American Airlines • Roundtrip • FirstClass
Price was $1,432, price is now $1,128 per person
$1,128
per person
found 22 hours ago
Loves this property. The staff was absolutely amazing and sooo helpful. I was not interested in the resturants so we did not eat them. It was close to everything downtown and we walked everywhere. Felt safe when walking. I loved the shower in the room! My only complaint would be that they don't have the ability to log into streaming services and that would prevent me from staying again. There wasnt even the ability to screen share.

Reviewed on Mar 22, 2026

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More About Flying To Brentwood from Chicago

Route Information for Flights from Chicago to Brentwood

Origin Airport IATA Code
CHI
Destination Airport IATA Code
BNA
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Brentwood

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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.